The story of music in 1999 is, in retrospect, two stories. On the one hand, MTV’s ’90s ascendance—a rise accelerated at the end of the decade by Total Request Live—precipitated the return of the single (and its accompanying music video) as the most important commercial product an artist could release. Artists best-equipped to market their sound with compelling visuals reached newfound levels of fame: the maximalist boy bands ’NSync and the Backstreet Boys, Britney Spears, Christina Aguilera, TLC, and rappers with enticing narratives and crossover potential like Jay-Z. And also some weirder phenomena: Lou Bega’s mambo revival, Eiffel 65’s all-blue-everything. TRL, and pop music in general, was a marketing machine—and the artists who were most marketable thrived.
At the same time, albums were still important—Napster had not yet delivered the death blow—and for more invested listeners, an important explosion and collision of genres was underway. Hip-hop was further and further expanding its market share in the mainstream; the grunge of the early ’90s had given way to a more accessible version dubbed pop-punk; emo was on the rise; indie music was having a renaissance; and bands like Rage Against the Machine, the Roots, and Nine Inch Nails were blurring the lines between genres.
Which is why, for The Ringer’s retrospective ranking of music in 1999, we decided to separate the singles from the albums—to fully encapsulate the depth, range, and utter weirdness of music 20 years ago. One other programming note: Only albums released in 1999 were eligible, while singles released in 1999 and ones that didn’t peak on the Billboard Hot 100 until 1999 were eligible. It only felt right to be able to recognize this guy and this guy at the same time.
Now, turn on Millennium—or, I guess, Willennium—and dive into one of the most interesting years of music ever.
What makes this song so good? UP-SIDE, IN-SIDE OUT! The hook of “Livin’ La Vida Loca” is massive, a catchy singalong that’s almost entirely responsible for the Latin explosion that took over American pop music in the years that followed. Two decades later, this song is perhaps regarded as a gimmick, but that probably says more about who we’ve become than about the song itself. Because “Livin’ La Vida Loca” still slaps.
Is this song a creative peak for Ricky Martin? Ricky had other hits—shout-out my “She Bangs” heads—but “Livin’ La Vida Loca” is his legacy as a musician. That’s not a bad thing. —Andrew Gruttadaro
What makes this song so good? “The Boy Is Mine” is the song people latched on to from Brandy’s sophomore album. It was doubtless a highlight, and so much fun, like a union between two culturally relevant singers fully dialed in tends to be. “Almost Doesn’t Count” by contrast is subtly devastating—the first line is “almost made you love me, almost made you cry.” And when Brandy sings to her hot-then-cold lover that they “can’t get to heaven half off the ground”? It’s like having a door slammed in your face.
Would this song be popular in 2019? There’s limited patience for lachrymose, piano-driven ballads on the pop charts nowadays, so I doubt “Almost Doesn’t Count” would make that many waves. —Micah Peters
Would this song be popular in 2019? Yes. With its soaring orchestrals, its earnest take on an absurd subject, and its unceasing commitment to the bit, “Thong Song” already possesses that “lol, is this for real? … Wait, actually, this is good” vibe of something sprung from the twisted minds over on TikTok. When Baltimore’s WTMD asked a disparate group of Baltimore musicians to create their own interpretations of the song in 2015, the results were a joyful, thong-clad romp through all sorts of genres. Shaq has been spotted singing the song at karaoke; a couple of other NBA players have admitted to putting the song on jukebox repeat to get a rise out of people. (I’m guessing this plan backfired when, instead, the exposure to greatness just made everyone’s day.) Even Sisqó himself still seems to like the “Thong Song”: He personally contributed to a 2017 EDM-y remix, and earlier this year, he honored his nearly two-decade-old work by personally performing it at his own wedding.
Is this song a creative peak for Sisqó? According to the artist himself, probably: In a 2017 interview with Billboard, Sisqó described “Thong Song” as “a bit of an anomaly” and admitted that “you can never write another one of those kind of songs.” Indeed, the single, which includes strings inspired by Wes Montgomery’s cover of “Eleanor Rigby” and a nod to “Flight of the Bumblebee” and is all about thongs, truly does have a feel all its own. Which is why it’s not surprising that Sisqó and “Thong Song” are often lazily assumed to be one-hit wonders, even if that’s also not totally accurate. For starters, years before Sisqóever crooned about dumps like a truck or rhymed “who’s the ish” with “devilish,” he was part of the respected hip-hop group Dru Hill. You know that Wild Wild West original motion picture theme song by Will Smith? Sisqó sang all those high notes in the chorus. And he was one of the writers of “How Many Licks?” that timeless Lil’ Kim celebration of candy consumerism and cunnilingus. “Thong Song” may be a peak, but Sisqó is a mountain range. —Katie Baker
Is this song a creative peak for Faith Hill? Yes. With respect to the cloud-bursting (and thesaurus-pounding) carefree rumble “This Kiss,” and the Diane Warren–penned Pearl Harbor torch song “There You’ll Be,” and Faith Hill’s countless other fine country-diva jams, yes, definitely, “Breathe” is her elegant and bombastic peak, with the delicacy of an origami crane and the indomitable might of a full tank battalion. The high note on “Baby isn’t that the way that love’s supposed to be” is eternal.
Would this song be popular in 2019 No, because country radio doesn’t play female artists anymore :( . —Rob Harvilla
Would this song be popular in 2019? Absolutely. While the Product G&B have not exactly repeated the no. 1 feat (“Maria Maria” spent 10 weeks there on the Billboard Hot 100), rap plus distinctive guitar riff equals success. Need proof? Just take a look at DJ Khaled’s “Wild Thoughts” with Rihanna, which remixed the “Maria Maria” riff and dominated airwaves for most of 2017.
Is this song a creative peak for Santana? No, but 1999’s Supernatural pulled Carlos Santana, then in his 50s, back into the present. The album’s conceit—Santana does Santana stuff while a motley crew of much younger artists do their thing by his side—turned out to be a huge success: The album took home eight Grammys, including Best Pop Performance by a Duo or Group with Vocal for “Maria Maria.” —Claire McNear
Many believe that “Maria, Maria” is not the best Santana song of 1999, that there is a “hot one” that stands above the rest. Kate Knibbs is one of those people; below, she and Claire McNear defend their Santana-related positions.
Kate Knibbs: I’m not saying “Maria Maria” is a bad song, but including it on this list while excluding “Smooth” is a chaotically evil choice that threatens to invalidate the integrity of the entire project. “Smooth” isn’t just one of the best singles of 1999, it was THE song of that year. Why are we pretending that “Maria Maria” mattered more? #JUSTICEFORSMOOTH
Claire McNear: This is, with all due respect, revisionist history. “Smooth” is great, don’t get me wrong—but “Maria, Maria” was a sensation. The song and its very many proper nouns were everywhere in 1999. And in 2000. It singlehandedly revived Carlos Santana’s career! Don’t let the memes and the late-internet popularity of “Smooth” confuse you—10 weeks at number one on the Billboard 200 can’t be wrong.
Knibbs: I’m not sure who is revising history here—not only was “Smooth” the first single that resurrected Santana’s career, but it spent two weeks longer on the Billboard charts! And I wouldn’t argue that “Maria, Maria” doesn’t deserve a spot on this list, but “Smooth” has had a much longer-lasting and entertaining cultural footprint. There’s a reason why DJ Khalid chose “Maria, Maria” as his Supernatural sample for “Wild Thoughts”—it would’ve been too obvious to resurrect “Smooth,” because “Smooth” never went away.
McNear: Ah, yes, samples are usually chosen specifically because their beats/killer guitar riffs are unmemorable. But OK, “Smooth” was a hit, too—but would Carlos Santana have caught on with the youths had he not been heralded in with “the sounds of the guitar played by Carlos Santana” (the words) followed by the sounds of the guitar played by Carlos Santana (the sounds)? Carlos Santana’s full name is mentioned five different times in “Maria, Maria.” It is the song that taught a generation to trust.
Knibbs: My take? Yes, Carlos Santana would have caught on with the youths on the strengths of “Smooth” alone, as it was a colossal international hit with formidable staying power. I’m not denying that “Maria, Maria” has its merits. But what makes it worthy of inclusion over “Smooth?!”
McNear: Short answer: Wyclef Jean. Medium-length answer: the Grammy award for “Best Pop Performance by Duo or Group with Vocal.” Long answer: It’s a freakin’ jam—and not just ironically, which is responsible for at least half of the song’s 159 million YouTube views (compared to the 241 million views of “Maria, Maria,” just saying).
Knibbs: In the words of Rob Thomas, “Give me your heart, make it real, or let’s forget about it.” And so I suppose we should agree to disagree and forget about this battle of Santanas. I’ll take solace in the fact that your take was, as they say, a hot one.
Would this song be popular in 2019—why or why not? I think so. It obviously includes some very outdated stuff—they call it a “cell phone!”—but the story of a good-for-nothing boyfriend spending all your money still resonates in 2019. “Bills, Bills, Bills” has a sense of humor, it’s fun, and it will always work.
What is the weirdest behind-the-scenes anecdote about this song? There is a response song called “Can’t Pay Your Bills” by the group Sporty Thievz, who went through a weird phase in the late ’90s in which they tried to piggyback on songs by female artists by creating responses from the male perspective. “Can’t Pay Your Bills” wasn’t actually their most successful effort, which was “No Pigeons,” a “No Scrubs” riff. Neither song is as good as the original. —Kate Knibbs
What makes this song so good? Much how Michael Abels flipped Luniz’s “I Got 5 on It" into nightmare fuel for Us, Havoc hurled Grandmaster Flash’s ’80s bop “White Lines (Don’t Don’t Do It)” down a dark project stairwell and turned it into a Queensbridge anthem. Paired with peak Prodigy verses—and eventually, those of Havoc and guest star Lil’ Kim on the remix—“Quiet Storm” embodied Mobb Deep’s trademark paranoia, only from a loftier perch. “Please don’t make me have to risk my freedom,” Prodigy pleads. They’re the sinister words of a man who finally has something to lose.
What is the weirdest behind-the-scenes anecdote about this song? In Prodigy’s autobiography, the late rapper described how he wanted to keep the song—originally titled “White Lines” and leaked to clubs and radio stations via DJ Clue—for his forthcoming solo H.N.I.C. album. But Havoc and Mobb Deep manager Chris Lighty eventually convinced him to give up the track as the first single for the group’s Murda Muzik album. —Donnie Kwak
What makes this song so good? A seven-minute, stadium-size breakup sing-along, “Tender” is the “Hey Jude” of the ’90s. Damon Albarn and Co. wrote the song as his relationship with Elastica’s Justine Frischmann was falling apart, and his low croon during the verses suggest a bad post-breakup hangover. But at the same time, “Tender” turns heartbreak into something communal, and thus bearable. “Come on, come on, come on, get through it,” the London Community Gospel Choir exhorts, while guitarist Graham Coxon joins in with a lovely countermelody. “Tender,” in the end, is bigger than a breakup: It’s an ode to getting by with a little help from your friends.
Is this song a creative peak for Blur? Did any rock band have a better, more creatively ambitious ’90s than Blur? (Please don’t say Oasis.) Like the rest of their masterful ’99 record 13, “Tender” is the culmination of a rich, wild decade that found the London quartet evolving from Brit-pop brats to art-rock heroes, from supposed one-hit wonders to ambitious album artists. “Tender” also strikes the perfect harmony between the band’s dueling songwriters, Albarn and Coxon; they could occasionally prove combustible, but on “Tender” they sound as balanced as yin and yang. —Lindsay Zoladz
What makes this song so good? The natural progression from an upbeat guitar lick at the top of the track to the full-on rock song it eventually becomes gradually brings “What’s My Age Again?” from vibe to jam to a genuine banger. By the time the chorus kicks in, your toe-taps have evolved into head bangs and jumps and flails. Throw in the fact that Blink offers a basic truth—“nobody likes you when you’re 23”—and you have the makings of a certified smash hit. Twenty-three isn’t really that old, but it’s not that young, and reckoning with the insecurities that come with having one foot in each pond is a universal experience.
Would this song be popular in 2019? Mark Hoppus’s opus on coming of age is as fitting now as it was 20 years ago. The idea of finding a sense of maturity—whatever that means—and being forced to reckon with poor choices made along the way is evergreen. The narrator openly admits his shortcomings by ruining an intimate moment with a girl, and then swerves head-on into reckless territory by prank-calling her mother. In the end, he’s left with a simple concession: Why would he ever want to act his age? —Shaker Samman
What makes this song so good? By 1999, Fiona Apple had earned a reputation as an arrogant rebel genius. Within the span of three years, she’d released an acclaimed debut album, won a Grammy, and publicly declared the music world “bullshit” in her acceptance speech. When it came time to make her second album, the sharp, reflective When The Pawn…, she was deep in the throws of an “it” relationship with another ‘90s brat prodigy: then-up-and-coming director Paul Thomas Anderson. “Fast As You Can” is a mad stomp meant to filter the ups and downs of a romance through an indecisive, troubled mind. Given that it was released at the peak of Apple and Anderson’s union—when they were most exalted and despised—it also seems to embody the breakneck pace at which these two were tackling their respective careers. Fiona was a high-profile rule-breaker who was madly, deeply in love with another high-profile rule-breaker, and every destabilizing moment in the song is a reminder of their legendary era-defining union.
What is the weirdest behind-the-scenes anecdote about this song? Anderson directed the “Fast As You Can” music video, using the same crew he employed for the production of his films. To make the whole thing appropriately jittery, he used a vintage hand-cranked camera, causing Apple’s mouth to be out of sync with the lyrics as she sings them. It’s all very painfully artistic and quirky. —Alyssa Bereznak
What makes this song so good? A top-tier ’90s slow jam, “So Anxious” finds Ginuwine perfectly capturing his anxiety waiting all night for a woman to call him back for a hookup. (Far more tense in the age of pagers, before we had “u up?” texts.) Producer Timbaland had been filling the airwaves with off-kilter hits for a few years by this point, but he played it straighter here—and the results were sexier than anything he had previously released.
Would this song be popular in 2019—why or why not? Drake basically made it a hit with “Legend” in 2015, so it stands to reason that “So Anxious” would still work. —Justin Sayles
What makes this song so good? I don’t know if the turn of the millennium was really a golden age for slow-dance songs or if I was just in middle school—and therefore going to school dances for the first time—in the time of boy bands and K-Ci and JoJo. But this is one of the best examples of the peak of the genre, dripping with rich harmony and adorable earnestness. From the finger-snapping to the strings to the very first the first guitar note to JC going up an octave in the last chorus, it is so committed to being a ‘90s slow-dance song, and that clarity of telos sets it apart.
What is the weirdest behind-the-scenes anecdote about this song? This isn’t behind-the-scenes, exactly, but it’s definitely weird. ’NSync was no stranger to collaborating with older artists—Richard Marx famously wrote “This I Promise You”—but having ‘70s country band Alabama release a contemporaneous cover of “(God Must Have Spent) A Little More Time on You” was, in the parlance of 2019, A Mood. —Baumann
What makes this song so good? Why fight over a boy when you can have an angel? After the success of the high-drama duet of 1998, Monica’s string of solo hits proved that she was so much more than just Brandy’s sparring partner. Most heavenly of all was “Angel of Mine,” a sweet, sophisticated ballad that was originally recorded by the British girl group Eternal. A crucial entry into the late-’90s slow-dance canon, the dreamy, swoon-worthy “Angel of Mine” remains a perfect showcase for Monica’s velvet voice.
Would this song be popular in 2019? A great ballad is timeless, so: Yes. But you know what would also be popular? Every single look in the music video. Just flawless. —Zoladz
What makes this song so good? There was a hard break between Janet Jackson’s sixth and seventh studio albums—1997’s The Velvet Rope represented a conscious uncoupling from her good-girl image and fully explored Janet, the Sexual Being. Busta Rhymes, meanwhile, was always more of a comedic figure than a sex symbol. But together, the two conspired to create one of the sultriest hip-hop singles, possibly ever?
What is the weirdest behind-the-scenes anecdote about this song? It’s not really that weird or behind-the-scenes or even that much of an anecdote, but I’d like to remind everyone that the Hype Williams–directed music video with Chrome Lava Busta beat the release of The Matrix by two weeks. —Peters
What makes this song so good?
Jay-Z’s highest-charting song to that point, “Can I Get A …” is a futuristic blast that solidified the rapper as a singles artist capable of delivering more than just dense street albums. Jay, Ja Rule, and Amil float on the Rush Hour soundtrack standout, delivering a call-and-response anthem that shot the two male rappers into a new stratosphere.
Is this song a creative peak for its artists? “Can I Get A …” was a commercial triumph for Jay and an important step on his path to world domination. But it wasn’t a peak for a man whose oeuvre includes Reasonable Doubt and The Blueprint. For Ja Rule, however, it was a star-making turn that gave him and producer Irv Gotti the runway to take flight for their greatest successes. —Sayles
What makes this song so good? “Miami” is great because it’s the platonic ideal of a big, dumb, poppy rap single, replete with imitable backing vocals where Smith’s uh-huh girls sing in a vaguely offensive Spanish accent. It’s engineered to be rap-sung in unison, in spite of yourself. For a time, like in the late ‘90s and early aughts, no one was touching Will Smith when it came to crafting these kinds of wildly bankable singles that were just the goofiest, but irresistible all the same.
Would this song be popular in 2019? I think pretty much every recent attempt by Smith at a comeback single indicates this probably wouldn’t work, but as a novelty single promoted through, like, TikTok? Who knows?! —Peters
What makes this song so good? Teddy Riley turned a Nickelodeon cartoon’s opening theme song into a black radio anthem. It was a corny, money-hungry moment which nevertheless proved how cool ’90s hip-hop and R&B could make, well, anything sound; yes, even The Rugrats Movie. The song is treacly, but smooth. The music video is goofy, but slick. Ma$e sold out, but he sold it so well.
Would this song be popular in 2019? In posterity, yes: “Take Me There” remains a karaoke standard for yours truly. —Justin Charity
What makes this song so good? Aside from being a glorious alternative-pop record with so much forward momentum it threatens to make your heart stop, “You Get What You Give” is an impressively prescient screed against corporate America, 1-percenters, and the world built by baby boomers and inherited by future generations. Songwriter Gregg Alexander was railing against “big bankers buying” a full 10 years before the recession.
What is the weirdest behind-the-scenes anecdote about this song? The climax of the song—in which Alexander directly threatens to beat up Beck, Hanson, Courtney Love, and Marilyn Manson—was a test, written to see whether the media would latch on to petty celebrity feuding rather than focusing on the song’s larger messages. Obviously, everyone failed the test. —Gruttadaro
What makes this song so good? It’s become déclassé to admit to liking Eminem. Too woke or too un-PC? Too weird or too mainstream? Too popular or too awkward? You know you’re overexposed when the world’s opinion of you exists across the polarity of all opinion. In retrospect, Marshall Mathers was neither vicious monster nor voice of a generation. He wasn’t the greatest rapper of all time, but he wasn’t a poseur white punk either. Somewhere along the way, Em became synonymous with controversy, and as his career grew, like all iconoclasts, he gave the iconographers what they wanted. I have a different perception of him, and think often of an alternate history. I like to think about a world in which Eminem became not the most famous rapper on earth. Maybe just the 14th- or 26th-most famous. “My Name Is” isn’t the best Eminem song (that will always be “Just Don’t Give a Fuck”) but it is the best song about meeting Eminem. “Hi kids, do you like violence?” The kid could write a lede.
Would this song be popular in 2019—why or why not? Of course. Carrying the imprimatur of Dr. Dre and the pop culture darts sold with every US Weekly subscription made him a palatable mainstream figure in 1999. But “My Name Is” is a deeply strange song (“Well since age twelve, I've felt like I'm someone else / 'Cause I hung my original self from the top bunk with a belt.”) that just happens to be a perfect pop confection. —Sean Fennessey
What is the weirdest behind-the-scenes anecdote about this song? Such a purist was then–Smash Mouth guitarist/principal songwriter Greg Camp that, after the band was implored to beef up 1999's Astro Lounge with a surefire hit that promptly became “All Star,” he originally included the line “Say bye bye to your soul,” which eventually had to be changed to “All that glitters is gold.” Your 10-year-old self was right: That line never did make sense.
Is this song a creative peak for Smash Mouth? Here I must confess: I am an unironic Smash Mouth fan (there are dozens of us; we meet on Tuesdays), and I am happy to tell you that no, “All Star” is emphatically not the best Smash Mouth song. It's not even the best song on Astro Lounge: "Defeat You," "Then the Morning Comes," and their "Can't Get Enough of You Baby" cover are all better (start to finish, it's a great sunny-day-in-the-park album—seriously). But in the years immediately following Astro Lounge, the band got mired in the wake of this song’s success and a few too many novelty songs; Camp eventually left, and that was pretty much that. Astro Lounge was as good as it got, and we should all be grateful. —McNear
What makes this song so good? The late ’90s were a golden age for the bonkers novelty hit, and few shone as bright as “Mambo No. 5,” Lou Bega’s ode to fedoras, women’s names, and THE TRUMPET. Was this the “Old Town Road” of 1999? I will leave you to answer that question.
Is this song a creative peak for Lou Bega? Lou Bega’s 2019 single “Scatman and Hatman” (which, yes, is a duet with fellow ’90s one-hit-wonder, the late Scatman John, that includes lyrics like, “Scatman and Hatman, traveling time/Scatman and Hatman, goin’ online”) would seem to prove that yes, it absolutely was. —Zoladz
What makes this song so good? Aside from the iconic “I like girls that wear Abercrombie & Fitch” line? Probably the hook at large, the smooth beat, the universal emotions tied to summer love, and the revolutionary realization on LFO’s part that boy bands could also be rap groups.
Would this song be popular in 2019? Hahahaha, HELL NO! Find me a teen who understands any of the following references from the song: Abercrombie & Fitch, New Kids on the Block, Larry Bird (“Jersey 33”), Willie Whistle, Alex P. Keaton, New Edition, Paul Revere, Fun Dip, Boogaloo Shrimp, Footloose, Billy Shakespeare. “Summer Girls” is of a time, and that’s just fine. —Gruttadaro
What makes this song so good? That opening guitar riff! The "nobody gets me" angst! The completely incomprehensible bridge! And also (and this time more seriously): that opening guitar riff!
Would this song be popular in 2019—why or why not? Not all of RHCP's oeuvre has aged well—a fact that band members would likely be pleased with, given how intentionally the early punk-funk jams were positioned as Not For Everyone. But 1999's Californication generally, and “Scar Tissue” (plus fellow single “Otherside”) emphatically, was crystallizing a grimy sort of alt-rock that still feels somewhat current today. —McNear
Would this song be popular in 2019? It better be! “Country radio doesn’t play female artists anymore” is unfortunately only a slight exaggeration, and if this fizzy and infectious and stridently odd crossover smash, more dance-pop than country and nearly more machine than man, can’t break the genre’s blockade, then there’s no hope for country music, or America for that matter. (Or Canada.)
What is the weirdest behind-the-scenes anecdote about this song? Shania Twain’s inimitable life and career is, for both good and ill, one endless, weird behind-the-scenes anecdote. But it still stands out that in 2017 she finally explained the “Okay, so you’re Brad Pitt!” line was, apparently, inspired by her unmoved reaction to Pitt’s appearance in Playgirl magazine: “I'm like, ‘Well, that don't impress me much,’” she told Billboard. “I mean, what is all the fuss. We see people naked every day.” God bless her. (And Canada.) —Harvilla
What makes this song so good? It’s a crystal-clear vocal performance from Whitney; the video look— strapless leather dress, no-nonsense bob, backup crowd of wronged women—is instantly recognizable. But it was the Thunderpuss remix, complete with that joyous “fool out of meeeeeeee” climax, that made “It’s Not Right But It’s Okay” a gay anthem and a runaway Billboard smash. Try not to dance to it.
Would this song be popular in 2019—why or why not? On the one hand, the methodology—printed credit card receipts, geographically-specific caller ID—is out of date. On the other hand, this is a song about receipts. “It’s Not Right But It’s Okay” was ahead of its time, my friends. —Amanda Dobbins
What makes this song so good? The sound of merciless, pitiless, machine-engineered rap. In other words, the sound of money. After the genre-changing success of The Chronic—an album so dusty with samples you could feel the residue on your fingers—and the humbling deflation of his Aftermath empire, Dr. Dre’s return was hugely anticipated. The album that ultimately came was billed as a sequel to his solo breakthrough, but there was hardly a dust mite in sight. Instead, this album, led by the electrified piano of “Still D.R.E.,” was resounding evidence of a technocratic rise in hip-hop. 2001—confusingly released in 1999—looked even further into the future, a world where EQ mattered more than what could be found while digging in the crates. Reuniting with his protégé Snoop Dogg, older and wiser and richer, Dre’s “Still D.R.E.” isn’t complicated—snare, kick-drum, hi-hat, plinking keys—but it sounds like it was designed on god’s very own KORG Triton keyboard. It doesn’t thump or rattle so much as it presides over us all, an emperor’s introduction. The century is ending, but fear not, the king has returned.
Would this song be popular in 2019—why or why not? Want to feel young? Dr. Dre is 54 years old. —Fennessey
Would this song still be popular in 2019? Absolutely, yes—the lyrics are essentially Instagram poetry! “Everything Is Everything” is basically Rupi Kaur verses elevated by Lauryn Hill’s voice and sweeping strings, making something that really does feel universal and true. Not only would the song be popular today, it’d probably pop up everywhere. “Everything Is Everything” is one of those songs that works in almost any situation; it fits just as well at a barbecue as it does in a yoga class, car commercial, or movie soundtrack. (Not that Hill would ever let it be in a car commercial.)
What is the weirdest behind-the-scenes anecdote about this song? This song was the first time John Legend played piano commercially! Still years before Chrissy Teigen arrived in his life, he was still an undergrad at the University of Pennsylvania, and performed under his birth name, John Stephens. —Knibbs
What makes this song so good? “He was singing it and saying shit like, ‘You was so in the pocket!’” That was Jay-Z, in 2001, talking about Michael Jackson’s reaction to the show-tune-sampling hit that turned Hov into a mainstream force. “I probably did that song in maybe five minutes,” wrote Jay-Z in Decoded. “I found the mirror between the two stories—that Annie’s story was mine, and mine was hers, and the song was the place where our experiences weren’t contradictions, just different dimensions of the same reality.” The result was a rap crossover so infectious that it even hooked the King of Pop’s ear.
What is the weirdest behind-the-scenes anecdote about this song? As explained in the “Hard Knock Life” oral history and in Decoded, the copyright holders of the Annie soundtrack originally denied clearance of the sample. So Jay-Z wrote a letter to the company explaining how he once won a seventh-grade essay contest that earned him a trip to see Annie on Broadway, and that the orphan’s plight immediately resonated with him. Cool story, but guess what: It was all a lie! —Kwak
Is this song a creative peak for The Roots and Erykah Badu? As singles artists, undoubtedly. The Roots very quietly have one of the largest and deepest and strangest and most adventurous catalogs in rap: They are album artists, at heart. (Go back to 2010’s How I Got Over, please.) But “You Got Me” is a gorgeous ballad that packs a full opera’s worth of energy and pathos into four minutes and change, a he-said-she-said short story worthy of Raymond Carver, and a bulletproof pop song that doesn’t skimp on the band’s radical adventurousness. (That drum-and-bass outro!) It’s the best of both worlds, meaning their singular and fearless planet, and also ours.
What is the weirdest behind the-scenes anecdote about this song? It is well known that Jill Scott co-wrote “You Got Me” with Scott Storch and sang on the original track, only for the Roots’ record label to insist on subbing in Erykah Badu’s vocals for the added star power. And if you want weird, and stupendously great, please revisit the wildly retooled live version the band flaunted during the 2005 film Dave Chappelle’s Block Party, featuring both Scott and Badu and going full psychedelic. It’s a chill-inducing moment when Badu joins the fray, but the space-cadet fray itself is, as always, a perpetual chill-inducer all its own. —Harvilla
Is this song a creative peak for Aguilera? “Genie in a Bottle” was Christina Aguilera’s post–Mickey Mouse Club breakout, her announcement to the world that she wasn’t just the cute kid folks saw on their TV screens. (And boy did she ever announce it: “Genie” includes lyrics like “you gotta rub me the right way” and “hormones racing at the speed of light.”) But this was Aguilera’s first real single; she didn’t write the song, and the people who did—David Frank, Steve Kipner, and Pamela Sheyne—admitted it was not an intellectual process. So, though her vocal contributions are amazing and this may be one of her most memorable performances, this wasn’t Christina’s creative peak.
Would this song be popular in 2019? Yes! The voice-overs in the refrain are undoubtedly corny (and the moany “ooooh oh oooh oh oohs” are really fun to mock 20 years later), and it’s certainly not what I’d consider “musically advanced” in 2019. But the message is overall pretty empowering, and I have to admit I had a hard time not bopping along to the refrain as I listened to it before writing this! It’s a tune that could use some updating, but the elements of a pop hit are all there, and it could still be a summertime smash today. —Megan Schuster
It’s time to dredge up one of the most prevalent arguments of 1999, because as the rule once went: When two other worldly talents arise at the same exact time, favorites must be chosen. None of us are Madonna—we cannot kiss both. Bringing this ‘99 debate into 2019 are the co-hosts of The Ringer’s podcast Tea Time, Kate Halliwell and Amelia Wedemeyer.
Kate Halliwell: Ah, Britney vs. Christina—the Taylor Swift vs. Katy Perry of years past, some say.
Amelia Wedemeyer: No one says that. You’re too young for this debate. Can I discuss this with a real adult? Anyone?
Halliwell: Too late, you’re stuck with me. Think of this as your chance to educate the youths!
Wedemeyer: Alright, if I must. Britney Spears is the clear winner of this debate– she was then, and she is now. Besides being an icon of American culture and the woman we all rallied around in 2007, Britney has been consistently churning out bangers for 20 years, and I do not think you can say the same thing for Christina. Honestly, name a song off one of the last three albums she put out: Bionic, Lotus, or Liberation. You can’t do it. Whereas you can with Britney’s last three albums: Femme Fatale (“Hold It Against Me,” “I Wanna Go,” “‘Til the World Ends”), Britney Jean (“Work Bitch,” “Perfume”), and Glory (“Make Me …”). Britney has a starpower that leaves us wanting more (cue the Chris Crocker’s “Leave Britney Alone!” video).
Halliwell: You’re not wrong—Brit’s catalogue of hits is much wider. But Christina’s vocals, Amelia! The vocals!
Wedemeyer: Okay, I will definitely give you that. But Britney’s talent is her ability to cultivate an intense following—people don’t just like her, they love her. She endures, and we have no choice but to stan.
Halliwell: I can’t pretend to have experienced the Britney vs. Christina debate in real time, since I was four years old in 1999. But I like to think this gives me a fresh perspective, from which I can see clearly that Christina Aguilera has had the far stronger late-career stretch! Yes, I’m now familiar with Christina’s chaps and Britney’s snake—but I’m honestly more familiar with Insta-Mom Britney and The Voice Coach Christina than I am with their ‘90s personas. And sure, while Britney may have been more successful back in the day, is she still?
Wedemeyer: Is she still? IS SHE STILL? UM, HELLO, while Christina was playing third fiddle to Blake and Adam on The Voice, Britney was headlining a Vegas residency. And let’s not forget about their respective social media presences. Britney has 56.4 million Twitter followers, while Xtina is sitting at 17 million; on Instagram, Britney has 22.3 million followers, while, yet again, Christina is lagging behind with 6.1 million. Numbers don’t lie, Kate.
Halliwell: Okay, I acknowledge that I may be in over my head here. But Burlesque is an all-time great guilty pleasure movie. Am I right? Is it just me?
Wedemeyer: It’s just you. Please go watch, like, a single Britney Spears music video and get back to me.
What makes this song so good? Beyoncé’s voice was still, shall we say, developing in 1999, but the specific, syncopated delivery of her “Say My Name” verses was virtuosic even then. (And the production of late-’90s R&B whisperer Rodney Jerkins fills the gaps.) The real magic here, though, is the punchy, three-word chorus that lends itself to even the most casual singalong. Beyoncé on lead vocals, and the rest of America on backup—a 1999 premonition of things to come.
What is the weirdest behind-the-scenes anecdote about this song? The vocals on “Say My Name” are performed by Beyoncé Knowles, Kelly Rowland, LeToya Luckett, and LaTavia Roberson. The video for “Say My Name” features Beyoncé Knowles, Kelly Rowland, Michelle Williams, and Farrah Franklin. And lest you forget, Luckett and Roberson learned they were fired from Destiny’s Child when watching the video, while reading the coordinated press release announcing the new lineup. It is a timeless hit and a lesson in music contracts, all in one song! —Dobbins
What makes this song so good? Mostly Ol’ Dirty Bastard’s line delivery of “I don’t have no trouble with you fucking me / But I have a little problem with you not fucking me.” And also “God made ’Dirt and ’Dirt bust ya ass.” And also “Sing it, girls!” (He means a young Kelis, who handled the hook.) And also “Eddie Murphy taught me that back at the house.” And also the way he rhymes Cristal with pist-als. And also everything else he says and the galactic exuberance with which he says it.
Would this song be popular in 2019? Absolutely. “Got Your Money” is both pure pop and pure anarchy, a pristine Neptunes beat and a mesmerizingly raucous performance from the single most raucous (and one of the most beloved) rapper of all time. This is the pinnacle to which all rough-hewn but clumsily mainstream-tilted SoundCloud rap aspires; it is to “Thotiana” or whatever what the sun is to a stick of butter. —Harvilla
What makes this song so good? Conventional wisdom would lead you to believe that technology is the playground of the young, but Cher’s never been one for convention. The ’99 mega-comeback hit “Believe” was a milestone for (at least) two incredibly different reasons: It made then-52-year-old Cher the oldest female artist to score a Billboard no. 1 song (a record she still holds) and it was also the first hit single to feature the then-emergent technology of Auto-Tune. “Believe” is at once an empowering post-breakup anthem and a meta-ode to the resilience of the almighty Cher. Bow down.
What is the weirdest behind-the-scenes anecdote about this song? Though those Auto-Tune’d vocals have become the signature attribute of “Believe,” the head of Cher’s label actually suggested that she nix the Auto-Tune when he first heard a version of the song. Cher’s response? “You can change that part of it, over my dead body.” Never, ever change, Cher! —Zoladz
What makes this song so good? When Lauryn Hill left The Fugees in 1997 to work on her masterpiece debut solo album, The Miseducation of Lauryn Hill, she also left behind a passionate, tumultuous affair with bandmate Wyclef Jean for a new romance (and son) with Rohan Marley. “Ex-Factor” was her recounting of that breakup, a vulnerable, soulful hip-hop ballad about love and pain that showcases both Hill’s vocal range and emotional depth. To say the song was an instant heartbreak classic doesn’t give it enough credit. Rarely does such honest songwriting make it into the Top 40, let alone reach the kind of omnipresence reserved for feel-good earworms. Twenty years later, the song is still being sampled and covered by everyone from Drake to Cardi B. “Ex-Factor” did that.
Is this song a creative peak for Lauryn Hill? Hill continued to explore the biblical themes of Miseducation on her 2002 live album, MTV Unplugged No. 2.0. And after that, she withdrew from the public eye, occasionally returning with stray singles, short tours, and a brief tax-evasion scandal. Though the media and her ex-bandmates have hinted that this hermitage may be due to mental instability, there’s also an argument to be made that it’s simply what happens when a bona fide empath becomes a world-famous pop star. (Between tracks on Unplugged, she tells the audience, “I had created this public persona, this public illusion, and it held me hostage.”) Miseducation remains her only studio album, and its standout track “Ex-Factor,” the very height of artistry. —Bereznak
What makes this song so good? The video for “Back That Azz Up” begins with a digi-slate countdown that functions, in full context, more like a timer for a bomb. I don’t know many people that don’t have a Pavlovian response to those massive, hollow opening strings. And besides Juvenile, I don’t know of anyone else bold enough to claim full ownership of the year 2000 in February of 1999. It is the most potent party record of all time—yes, of all time—and just as viable in the club as it is at a pool party, a family reunion, or even a baby shower, provided you opt for the edited version. But if you do play the edited version, know that you are a coward.
What is the weirdest behind-the-scenes anecdote about this song? Juvenile had been performing the vocals to “Back That Azz Up” in clubs for nearly two years by the time the single was released. Mannie Fresh laid the production ad-hoc, and the iconic violin strings were dropped into the mix specifically to capture white America. In a 2014 interview with Complex, Fresh shared that he knew they struck diamond with “Azz” when Sharon Stone said it was her favorite song. So there you have it. “Back That Azz Up”: Sharon Stone’s favorite song. —Peters
The most important thing to understand about the music of 1999 is that it was conceived, written, and produced under sociopolitical conditions the likes of which we may never see again. American history is one nearly unbroken chain of warmongering and economic disasters, as The Greatest Country In The World™ clangs from one crisis to the next. There have been two brief stretches in which there was no existential threat hanging over the nation—at least since 1900, maybe ever. The first was the Roaring Twenties, and the other was the brief interregnum between the end of the Gulf War and the presidential election crisis of 2000.
That’s not to say that there weren’t any problems, but that they felt manageable, and hundreds of millions of people, liberated briefly from the threat of annihilation, behaved with optimism. Business and culture alike thrived, the information revolution boomed, and Toronto rock group Len released a mostly-joking single that featured nonsense lyrics and sampled heavily from Andrea True Connection’s “More, More, More.” They famously spent most of the music video budget on booze, so much of it that they broke the elevator at their hotel trying to lift it.
The result? The greatest cultural artifact of the final moment of optimism in American history, four minutes and 26 seconds of bouncing, lighthearted, unapologetically unserious glee that hops from the Sunday morning grass to a park bench slide to a perky borrowed piano ditty. It is not cool, nor does it particularly aspire to be cool—it just came about in a time and place where that didn’t matter. “Steal My Sunshine” is what it sounds like to be truly lost in unadulterated happiness. Or so I’ve been told. I wouldn’t know what it’s like to be truly lost in unadulterated happiness: I came of age in the 2000s. —Baumann
Max Martin has created many sticky earworms in his lifetime, but “I Want It That Way” is pop music Gorilla Glue. The power of the mid-tempo single that leads the Backstreet Boys’ third album, Millennium, is in its buildup. The song starts softly, with a gentle, Metallica-inspired guitar riff, and—with the collaborative teamwork of AJ McLean, Howie D., Kevin Richardson, Brian Littrell, and Nick Carter—grows more dramatic with every gushing, nonsensical lyric. Against the backdrop of an LAX hangar, these boys work hard to deliver the message, even if they know there isn’t really a message at all. But in the same vein of, say, “Zendaya Is Meechee,” the lack of meaning in “I Want It That Way” somehow enhances its singability. Before it’s through, it has infected your brain, and convinced you to belt out that emotional “DON’T WANNA HEAR YOU SAY” crescendo right alongside lead hunk Carter.
It’s this theatrical passion, combined with an absurd hollowness, that has made “I Want It That Way” the “Don’t Stop Believin’” of the millennial generation. Everyone from One Direction to Charlie XCX has covered it. And it’s a karaoke entry so universal that it once brought Kanye West and Mark Zuckerberg together. “I Want It That Way” taught us that things don’t have to make sense to be good, and I honestly wouldn’t have it any other way. —Bereznak
Think of “Heartbreaker” as a sublime moment in time in which two artists heading in different directions met to produce a song that, 20 years later, still feels essential.
On the one hand, there’s Mariah Carey, perhaps the biggest star of the ’90s, closing out the decade with a song that, while perfect in a timeless sort of way, was baldly a reproduction of past hits. Not that that’s a bad thing: At the time, critics lambasted Mariah for sampling Stacy Lattisaw’s bubbly “Attack of the Name Game” the way she sampled Tom Tom Club’s bubbly “Genius of Love” on 1995’s “Fantasy” (some critics even assumed that the same sample was used for both songs, such was life pre-internet), but you can’t ignore the results. “Heartbreaker” is undeniable and everlasting, an apt sendoff for Mariah’s youthful persona as she transitioned into being one of the more mature singers in the room. (Surely, there is a smart essay to be written about Mariah ushering in a new era by fighting herself in the music video for “Heartbreaker,” but we don’t have time for all that right now.)
On the other hand, there’s Jay-Z, ascending to his throne as the best, most bankable rapper of his generation. By the time “Heartbreaker” was released, Jay had already dropped “Hard Knock Life” and “Can I Get A…,” two songs that spoke to the rapper’s mainstream bona fides. But “Heartbreaker” proved how well Jay’s style and persona mixed with female singers, the way he could play off a woman’s strength and sincerity with boyish bravado and deft flow (his “She wanna, pillow fight in the middle of the night” bar on “Heartbreaker” remains an all-time earworm). To say that this dynamic would go on to be successfully reproduced would be an understatement. In fact, Jay’s life—and the arc of his career and a certain other female musician’s career—was forever changed by it.
So maybe “Heartbreaker” is best as a time capsule. But I’d also argue that it’s simply best as a damn good pop song. —Gruttadaro
Just so there’s absolutely no confusion, Chili begins with a definition:
scrub (noun): 1. a guy who thinks he’s fly 2. someone who is always talking about what he wants but then sits on his broke ass (see also: busta)
And now you know. “No Scrubs” is a kiss-off song so withering, so methodical, so specific (have you ever stopped to appreciate how vivid an image “hangin’ out the passenger side of his best friend’s ride” actually is?) that there can be no adequate response to it. Some have tried, of course—there was a song called “No Pigeons.” But do you remember “No Pigeons”? Exactly. Moving on.
“No Scrubs” is the crown jewel of TLC’s third album, Fanmail, a futuristic pop odyssey that would, unfortunately, become the final TLC record before the untimely 2002 death of Lisa “Left Eye” Lopes. (May she rest in power, unbothered by scrubs in heaven.) And so for all its buoyant sass, there’s something elegiac about this song in retrospect: “No Scrubs” and its iconic Hype Williams–directed video would become one of the last living statements from one of the defining girl-groups of the ’90s. If the question was what about your friends? the answer, of course, was TLC.
While it’s a little lacking in the “T,” “No Scrubs” was Chili’s moment to shine—it was, at that point, the only TLC single on which Rozonda “C” Thomas sang the verse’s lead vocals. But their voices all come together on that unforgettable chorus—a looping, singsongy indictment of deadbeats the world over. The message of “No Scrubs” is timeless: It is ultimately an ode to raising your standards, having your friends’ backs, and never settling for less than tender, loving care. —Zoladz
A perfect pop song should transcend all time and reason, but there are commonalities among them if you care to look. A memorable rhythmic hook—say, three piano notes smashed so loudly they become a threat. A short, singalong snippet of chorus—first-person and vowel focused if possible (for maximum shrieking), and ideally involving an adlib of some kind (for group singing). You’ll want a music video that upends teen fashion and upsets parent groups; you’ll need a music industry on the brink of disaster, or at the very least a media machine willing to bank their success—and their flagship TV program—on yours. It helps to find someone who can handle the choreography.
By any numeric standard, “...Baby One More Time” is an obvious best song of 1999 pick—the single sold millions of copies, it dominated Total Request Live, it reached No. 1 on the charts in multiple countries. It is the convenient “music narrative” pick: post-grunge, pre-Napster, the glossiest achievement of a hyper-controlling industry on the brink. Happily, it is a pure pop masterpiece, and according to this list, Max Martin’s single greatest producing achievement. But “...Baby One More Time” is also a time capsule—of an ascendant Britney Spears; of unexamined fame; of bubblegum pop; of life before the internet; of millennials, god help us, coming of age. It launched a star and eventually ended an era of stardom. It was a musical triumph and a tipping point all in one. So was 1999, it turns out. —Dobbins
What makes this album so good? 1998’s Still Standing was largely an extension of the sound that captured a small but dedicated fan base on 1995’s Soul Food. World Party was Goodie Mob’s first album not entirely produced by Organized Noize—and their first deliberate attempt at commercial viability—and while not all of the tailor-made-for-radio stuff comes off, it’s intriguing to hear the group work with different producers. Some of it even works.
What is the key song on this album? “Rebuilding” is the song on this project that sounds most Goodie Mob, which is important considering they went out of network for the production. D-Dot is the credited producer, but here’s the thing: The popular myth is that the song was actually entirely produced by his apprentice, a young Kanye West. —Micah Peters
What makes this album so good? The album’s third song, “Helps Both Ways,” begins with a short clip of a play-by-play announcer detailing a screen pass in a football game before the slow plucks of a guitar string ever begin. As the call continues, the melancholy tones drive on while slow, deliberate drums kick in. Things stay that way for much of the song, and while the combination may sound sparse, what it accomplishes is anything but small. Listening to “Help Both Ways” conjures an image of a man, lit only by his television, empty Chinese food cartons strewn across the table. Come on Die Young’s brilliance is in how much it can evoke with so little.
What is the weirdest behind-the-scenes anecdote about this album? The opening track, pointedly titled “Punk Rock,” consists of Mogwai playing over a clip of Iggy Pop answering a question about what he considers the essence of punk rock. “You see,” Iggy says, “what sounds to you like a big load of trashy old noise is in fact the brilliant music of a genius, myself.” It’s a tone-setting commentary on the self-serious reputation that the Scottish post-rockers had developed early in their careers, but it also served as a perfect setup for the path this record was about to carve. By the way, the clip is from a 1977 Canadian Broadcasting Company interview. —Robert Mays
How does this album serve as a defining moment for music in 1999? Millenium set a U.S. record for shipping 11 million copies of an album in a single year and was the best-selling album of 1999. It charted four Top 40 singles and launched an international tour. Its rollout also came with a handful of international CDs that contained bonus tracks, the perfect way to sucker 11-year-old me into spending all of my allowance at the local Sam Goody. The album’s fast-produced Max Martin poppiness and commercial success embody a time when the music industry was rollicking Scrooge McDuck–style in piles of cash, before iTunes came along and completely upended the industry as we knew it.
What is the weirdest behind-the-scenes anecdote about this album? Max Martin introduced the album’s breakout single, “I Want It That Way,” to the Backstreet Boys during their two-week recording trip to Stockholm in November 1998. Two days after they left Sweden, they completed the song's vocals. It was the pop music equivalent of a McDonald's Happy Meal: fast, cost-efficient, and shamelessly satisfying. —Alyssa Bereznak
What makes this album so good? The last in a trilogy of peak ’90s alternative rock albums, This Desert Life is a continuation of Counting Crows’ odd mix of melancholy, desperation, and upbeat optimism. Counting Crows albums always relied on the strength of their standouts—from “Mr. Jones” defining August and Everything After to “A Long December” doing the same for Recovering the Satellites—and This Desert Life had a couple of big ones in the raucous “Hanginaround” and the profound “Colorblind.”
What is the weirdest behind-the-scenes anecdote about this album? For the climactic sex scene in Cruel Intentions, director Roger Kumble was planning to use “To Sheila” by the Smashing Pumpkins until lead singer Billy Corgan pulled out. “And then somebody said, ‘Hey, Adam Duritz saw your movie and really likes it,’” Kumble told The Ringer. “‘They’re working on a song and think it could work. They’re cutting it tonight at their house. You wanna go by?’ And I was like, ‘Fuck yeah.’” And that, my friends, is how “Colorblind” ended up in Cruel Intentions. —Andrew Gruttadaro
What makes this album so good? Big-time hip-hop collaborative albums don’t always work out—for every Watch the Thrones, there’s a Huncho Jack, Jack Huncho. Redman and Method Man’s first full-length collab, Blackout!, could’ve fallen into the latter category as a quickly forgotten novelty project capitalizing on their shared love of weed and a minor hit from four years prior. Instead, the two sound like kindred spirits as they trade punch lines and finish each other’s ad-libs over some of the liveliest production either had ever graced.
How does this album serve as a defining moment for music in 1999? Blackout! solidified the pair as rap’s charismatic, lovable stoners—no small feat considering one had once famously bragged about all the things he’d do to you with a spiked bat. Their new image would pay off in the following few years in the form of movies, TV shows, and the best episode of Cribs to ever air. —Justin Sayles
What makes this album so good? A struggling rapper turns to hustling to bankroll his fledgling music career—the story has been told countless times in hip-hop, but never like this. Fresh off a critical reappraisal following 1996’s Psychoanalysis: What Is It?, superproducer Prince Paul convinced Tommy Boy to release his boldest idea yet, a 77-minute movie on wax that follows a young rapper named Tariq through the criminal underworld. There, he meets a zany arms dealer (Kool Keith), a racist cop (a pre–Whitey Ford Everlast), a pimp named Count Macula (Big Daddy Kane), and, of course, junkies (Chris Rock and De La Soul). But the anchor is a young Breezly Brewin, the sharp-tongued New York MC who brings the rap opera to life as Tariq.
How does this album serve as a defining moment for music in 1999? At a time when the “independent-vs.-mainstream” debate was at a fever pitch, A Prince Among Thieves showed that underground hip-hop was capable of more than just loosie 12-inches and punch line raps. But of course it makes sense that the man who invented the rap skit would craft one of the more ambitious concept albums the genre has ever seen. —Sayles
What makes this album so good? How shocking it was at first contact. By 1999, the Flaming Lips had spent 13 years as anarchic and drug-fueled Oklahoman noise-rock icons, flirting with pop success in the alternative-nation ’90s (see their delightful fluke hit “She Don’t Use Jelly”) but never getting close to the cuddly-psychedelic orchestral bombast that bowled you over 10 seconds into Soft Bulletin opener “Race for the Prize.” It was Pet Sounds for pre-millennial art-pop pranksters in animal costumes, beautiful and gigantic and shocking, and as thrilling a single-album reinvention as any in rock ’n’ roll history this side of David Bowie.
What is the key song on this album, and why? “The Spiderbite Song” is a very sweet and delicate piano-and-concussive-drum ballad that also addresses, in barely metaphorical language, multi-instrumentalist and core member Steven Drozd’s debilitating heroin use. It’s a singular combination of easy on the ears and hard on the heart: “I was glad that it didn’t destroy you,” frontman Wayne Coyne cheerily wails. “How sad that would be / ’Cause if it destroyed you / It would destroy me.” —Rob Harvilla
What is the weirdest behind-the-scenes anecdote about this album? MF Doom was born Daniel Dumile and formerly known as Zev Love X, part of the rap group KMD. KMD was dropped by Elektra Records before the release of their sophomore album, and around the same time, Dumile’s brother Subroc died in a tragic accident. He originally hatched the MF Doom alter ego to take revenge on an industry, and a world, that had broken his spirit.
What is the key song on this album? “Rhymes Like Dimes” has a hook that spans an entire verse, and some of Doom’s most inspired lyrical miracle-ing: “Only in America could you find a way to earn a healthy buck and still manage to keep your attitude on self-destruct.” —Peters
What is the key song on this album, and why? It’s gotta be “I Try,” the album’s propulsively huge hit, which won Gray her first Grammy and remains her only song to reach the Top 40. There is something really alchemical about “I Try,” even if Gray never struck gold like this again. The lyrics are plaintive and almost futile, but they’re paired with an anthemic melody played on a big booming organ, making the song sound hopeful and utterly resigned to despair at the same time.
What makes this album so good? On How Life Is is the answer to a question no one asked: What if Fiona Apple’s and Prince’s music had a baby who sang like Billie Holiday with a head cold, and it absolutely ruled?
Most people know Gray from this album’s biggest hit, “I Try,” which is fair, because it’s a killer anthem—but On How Life Is, like Alanis Morissette’s Jagged Little Pill, is one of those preposterously assured debut albums with a lot more going for it than its breakout single. “I Try” got most of the attention, but for my money, “Still” is one of the most genuinely moving songs of the late ’90s, a rueful, painfully tender lament about an abusive relationship. And Gray knew how to have a good time, too—“Why Didn’t You Call Me” and “I Can’t Wait to Meetchu” are bluesy bops, “I’ve Committed Murder” is the ska revival’s best song no one noticed, and the rest of the album, including “Sex-o-matic Venus Freak,” is funky and weird and funny. Gray didn’t deserve her one-hit wonder status, and On How Life Is has been bizarrely neglected for way too long. —Kate Knibbs
What makes this album so good? That would be Tom Waits’s voice, a surrealist barnyard menagerie of bluesy growls and torch-song croons and jazz-demon screeches poised precisely halfway between vaudeville and Hades. By 1999, Waits had spent 25 years as a songwriter’s songwriter and a weirdo’s weirdo, but Mule Variations was a shock in terms of both its craggy beauty (piano ballads like “House Where Nobody Lives” and “Picture in a Frame” are all-timers) and its menacing and beguiling weirdness. The eerie spoken-word tour de force “What’s He Building?” is an all-timer too, so far as freaky neighbors go, but good luck trying to out-freaky this guy.
What is the weirdest behind-the-scenes anecdote about this album? The weirdest ones, we’ll never know. But for the uninitiated, the first 15 seconds of opening track “Big in Japan,” wherein our man beatboxes with unsettling aplomb, are a fine introduction to the Tom Waits experience. “I was in Mexico in a hotel, and I only had this little tape recorder,” he recalled. “I turned it on, and I started screaming and banging on this chest of drawers really hard, till it was kindling, trying to make a full sound like a band. And I saved that. That was years ago. I had it on a cassette, and used to listen to it and laugh. It sounded like some guy alone in a room, which it was.” —Harvilla
What is the key song on this album? Undoubtedly, the domestic-violence revenge fantasy “Goodbye Earl,” penned by deified country songwriter Dennis Linde, with a defiantly silly video starring Jane Krakowski as the abused woman who ensures you’ll never look at black-eyed peas the same way again. It’s a stupendously upbeat approach to a grim topic, and it triggered a sizable controversy the group reveled in from the start. “The Dixie Chicks do not advocate premeditated murder,” they wrote in Fly’s liner notes, “but love getting even.”
How does this album serve as a defining moment for music in 1999? Fly was the Dixie Chicks’ second diamond-selling album in as many years (after 1998’s Wide Open Spaces), a pop-country crossover behemoth echoing the huge success of Shania Twain, Faith Hill, and a host of other country stars, from Martina McBride to Jo Dee Messina, who’d struggle to get half the airplay in today’s super-macho Nashville. 1999 is a utopia in retrospect, in terms of how the industry would come to treat female country artists and how America would come to treat the Dixie Chicks. Crank up “If I Fall You’re Going Down With Me” and try not to get too depressed. —Harvilla
What makes this album so good? In 1999, it wasn’t easy being weird in rap. Take Prince Paul: Despite success with De La Soul and Gravediggaz, the producer had receded to the genre’s fringes by the middle of the decade, crafting trip-hop album and rap operas while his peers chased chart success. Also operating on those fringes: Dan the Automator, best known for helming Kool Keith’s psychedelic masterpiece Dr. Octagonecologyst. Introduced by a mutual acquaintance, the pair bonded over their love for Chris Elliott’s Get a Life, pulled out their Rolodexes of alternative and indie rap demigods, and created the ultimate dorm room album of the late ’90s.
What is the weirdest behind-the-scenes anecdote about this album? One day in the middle of recording, Dan the Automator showed up to dinner to meet a friend, who had brought along legendary SNL comedian Don Novello. Automator convinced Novello to come to the studio that night and record skits as his famous Father Guido Sarducci character. The tinted-glasses, chain-smoking priest became a comedic anchor on an album built around comic relief. —Sayles
What makes this album so good? Hindsight. The duo of Jack and Meg White seemed to appear out of nowhere in 1999, and were more or less treated as such. Their breakthrough, 2001’s “Fell in Love With a Girl,” would have to wait a few years. But this first album, cheaply recorded and released to little fanfare, is like a Luis Castillo sinkerball—hard, heavy, hot, and bound to dive at any moment. It presages a return to scuffed-up guitar heroism, but with its coy ballads and a choice Bob Dylan cover, it flashes a little soul, too. Jack’s guitar-playing is a tangle of influences—the Stooges, Son House, Jimmy Page—that becomes tensely wrapped around Meg’s thud...thud...thud-thud-thud drumming style. And when he cuts loose—see the absolutely blazing “Cannon”—you can hear the early signs of that unique blend of the savvy and the spiritual that would eventually make him the axe slinger of his generation.
How does this album serve as a defining moment for music in 1999? It really doesn’t represent anything about 1999—neither the indie rags nor the mainstream rock press quite knew what to do with these color-coordinated candy cane weirdos. That would soon change. —Sean Fennessey
What makes this album so good? For her fourth album, the Queen of Hip-Hop Soul leaned further into the latter part of her moniker, transitioning away from rap beats into a more grown-folks version of R&B. Gone were feature guests like Lil’ Kim, Nas, and the Lox, replaced by Aretha Franklin, Elton John, and Eric Clapton. Mary wasn’t turning her back on her roots; instead, she simply confirmed the universal power of her voice. It was the legends on Mary, after all, who were the invited guests. Mary was right at home.
What is the key song on this album, and why? The previous year, Mary collaborated with Lauryn Hill on a song called “I Used to Love Him” for The Miseducation of Lauryn Hill. Hill returned the favor by writing and singing backup on the Mary album opener “All That I Can Say.” It’s a classic Mary love song: fearlessly open-hearted but oh so vulnerable. Lauryn added an intro rap when the two performed together on The Queen Latifah Show.—Donnie Kwak
What makes this album so good? It is objectively beautiful, and the ways in which one interfaces with that sensory beauty is not dissimilar to how one takes in a David Attenborough documentary: with an uncomplicated sense of wonder. Every component—from the ambient whirring, the way clarion keys ripple through the waves of string instrumentation, the sound of lead singer Jónsi’s voice sublimating amid a spine-tingling symphonic spree, the glacial post-rock-ness of it all—conveys a vastness to an imagined landscape. Ágaetis Byrjun is a feat of world-building that has few equals in the 20 years since its inception.
What is the key song on this album, and why? “Starálfur,” a song that has never been discussed without using the word “cinematic.” The piano that emerges from the swelling strings just before the 20-second mark is one of the most indelible moments of the past two decades in music. It’s the sound of mountain ranges forming in a time lapse; it ascends and flourishes. Just before the three-minute mark, everything drops but Jónsi’s voice and a strumming acoustic guitar. The mountains recede. It’s a soft snap back to reality, a brief intermission for the guitar-wielding bard. Soon enough, the piano returns, and off again we go into the expanse. —Danny Chau
We know how staffers of a certain age feel about the music of 1999, but how does it sound to someone who was barely a toddler by the time Y2k hit? To find out, we forced Mose Bergmann, 25, to listen to a selection of the albums on this list, and then asked him several questions.
What are the five adjectives you’d use to describe 1999? Angsty. Monogamous. Frumpy. Immediate. Jacketed.
2. Which 1999 lyric made you raise your eyebrows the most? All the Fist-a-gons, the bullets, and bombs / Who stuff the banks, who staff the party ranks / More for Gore or the son of a drug lord / None of the above, fuck it, cut the cord!
As someone who’s recently been trying to find the VPN that’s right for me, when Zack De La Rocha said, “cut the cord,” I felt that.
3. Please explain Sigur Ros. Listening to Agaetis Byrjun was my first real exposure to Sigur Ros (besides The Life Aquatic); I was surprised to learn they are not, in fact, Bjork. I feel like this album is what you get when you finally get internet after gazing at the majesty of the Icelandic countryside for too long. Every song sounds like either an intro or an outro.
4. Which, if any, currently popular musicians are the Most 1999? I feel like Maggie Rogers could fill a Fiona-Apple-type slot in ‘99. Denzel Curry’s incredible Rage cover makes me think he could thrive. Or maybe Lil Nas X? Joking, but could you imagine?
5. Which 1999 album is best suited for TikTok? And why? A fundamental feature of many successful TikToks is soundtrack dissonance, when somebody’s going hard to a song that just does not fit. So, as The Ringer’s resident youth correspondent and TikTok expert, I feel like the pure enigmatic sincerity of Agaetis Byrjun is the perfect soundtrack to hit the woah to.
What is the key song on this album, and why? The album opener, “Stacked Actors,” with its whispered, growled, and screamed vocals, and dominant bass line, feels like Foo Fighters trying on a borrowed shirt. You can’t get from that to “Learn to Fly” and “Gimme Stitches” without a bridge, and “Breakout” signifies the end of the preamble and the beginning of the main course.
How does this album serve as a defining moment for music in 1999? Music evolves, and the blurring and blending of genre and technique has led to marvelous moments. Moreover, the rockism of the 20th century is being interrogated, identified as toxic, and dismantled bit by bit. But goddamn, the basic four-piece rock band was great. They no longer make—or at least they don’t praise—the kind of post-punk, post-grunge crunchy guitar tone that defines this album, and that defined rock in the 1990s. —Michael Baumann
What is the key song on this album? The up-tempo cheer of “I Think I Need a New Heart” will warm you—at least until you listen to the lyrics.
How does this album serve as a defining moment for music in 1999? It’s easy to write off 1999’s breakthroughs as purely the province of pop-inflected hip-hop, pop-inflected country, pop-inflected punk, pop-inflected ska, and, well, plain old bubblegum pop. But the Magnetic Fields spent the year getting weird. 69 Love Songs is what it says it is: 69 (nice) different love songs, each written by the Magnetic Fields’ Stephin Merritt. Not all of them are great, or even good. But plenty are, and they both echo the best (non-pop) tunes from earlier in the ’90s, and presage the coming wave of indie rock that would sweep through the industry just a few years hence, washing out much of the bubblegum with it. —Claire McNear
What makes this album so good? It’s Pavement. I’m not trying to be funny, but the worst Pavement album (Terror … was the band’s fifth and final full-length) is better than most bands’ peak. This was the sound of a band that was more than ready to wrap things up, but not before they offered a few more quintessential pieces of languid indie rock. “Spit on a Stranger,” “Major Leagues,” and “Billie” are some of the catchiest melodies Stephen Malkmus ever penned, and jams like “Platform Blues” and “The Hexx” find him tipping toward the free-form psychedelia that colors a lot of his solo work. Whether he’s hanging loose or keeping it tight, it’s still Malkmus, which means you get travelogues like this: “Senior year abroad / I ripped the pea out of the pod / In store for three months of exile in Spain / Where was the danger? / Watch out for the gypsy children in electric dresses, they're insane / I hear they live in crematoriums and smoke your remains.”
What is the weirdest behind-the-scenes anecdote about this album? No one could quite agree on how to make it. Nigel Godrich, coming off critically acclaimed productions of Radiohead and Beck, wanted to work with Pavement so badly he was willing to sleep on a friend’s floor in NYC to make it happen. The band and producer pinballed around costly studios in New York and London, looking for the right sound, only to wind up with an album that no one was quite happy with. Godrich envisioned a stoner rock record, the band wanted something that was a bit easier listening, and it cost them $100,000 to reach an unhappy compromise. Pavement would break up before the end of 1999. —Chris Ryan
What is the key song on this album, and why? “Got Your Money.” It’s not the best song, though it’s still probably ODB’s best known, an early star in the Neptunes galaxy of hits, and one of the first appearances of a young singer named Kelis. “Got Your Money” has an Is this a bit? charm that suffuses the entire album—rambunctious and almost parodic, from the Rick James– and Dolemite-style gags that dot the album to ODB’s operatic, off-key wailing. Gone are the crackling, jagged edges of 1995’s “Brooklyn Zoo,” replaced by something more slick, less naturally ODB. And yet, it remains one of the signature Wu-Tang songs, perhaps the group’s commercial pinnacle. The contrast stretched the definition of pop stardom, taking ODB out of the shadows and establishing the prankster-jester persona that would trail him until his death. “Recognize I’m a fool and you love me!” What is the weirdest behind-the-scenes anecdote about this album?
The video for “Got Your Money” features no new footage of ODB, as he had returned to prison before it was scheduled to shoot. Instead, it’s intercut with archival footage of Dirty and several sequences from Rudy Ray Moore’s blaxploitation comedy Dolemite. —Fennessey
What makes this album so good? A bleak but oddly stirring meditation on mortality, the prolific folk songwriter Will Oldham’s first album as Bonnie “Prince” Billy is one of his long career’s crowning achievements. These 11 songs are intimate nocturnal murmurs, animated by a generosity of spirit that can make a song called “Death to Everyone” feel not like a punishment so much as a communal rite of humanity.
What is the key song on this album? The deeply moving title track has rightfully become a modern American standard—thanks in part to Johnny Cash’s 2000 cover, on which Oldham himself had the honor of singing backup. —Lindsay Zoladz
What makes this album so good? “The return of John Frusciante” is certainly the simplest answer to this question, but in more detail: Californication feels like the Red Hot Chili Peppers finally realizing their mission statement, and ascending accordingly to the throne atop late ’90s rock.
What is the key song on this album? Maybe it’s too obvious to pick the title track, but “Californication,” with its gliding, dripping Frusciante riff and its Anthony-Kiedis-as-dismal-tour-guide lyrics (and its absurdly ’90s music video) is what this album is all about. —Gruttadaro
What makes this album so good? The Fragile’s enduring quality is the sheer amount of gall it required to even attempt, let alone execute. Five years after the release of The Downward Spiral, Trent Reznor created a sprawling double album with a soundscape whose scale and breadth can confound, overwhelm, and stagger. Even the “quieter” tracks on The Fragile, songs like the piano-driven “La Mer,” are constantly building and piling on layers as they hurtle toward an emotional crescendo. There’s a reason that “The Mark Has Been Made” works so well as the backdrop for Denzel Washington preparing to wreck shit in Man on Fire. The Fragile is visceral, its grandeur cinematic. It remains the most ambitious work of an artist defined by unfettered ambition.
Would this album be popular in 2019? Probably not. The Fragile’s debut at no. 1 in 1999 is a peculiar artifact from a long-gone era. There’s no “Closer” on this album, none of the synthy dance grooves from Pretty Hate Machine. But to say The Fragile wouldn’t be popular in 2019 isn’t to say it wouldn’t be relevant. A track like “Just Like You Imagined,” driven by Mike Garson’s entrancing piano work, is a clear precursor to the work Reznor would do as an Oscar-winning film composer. —Robert Mays
How does this album serve as a defining moment for music in 1999? Missy was more assured on her sophomore project, and she and Hype Williams together fashioned a whole new image of femininity—it was powerful but desirable and so alien as to make it impossible to look away from. “You may get females (that) want to look nice, they want to look glamorous in their videos, as opposed to me, I’m like, whatever,” Elliott told Reuters in 1999. No one in hip-hop had ever been so free in expressing themselves.
What is the key song on this album? “She’s a Bitch,” which anchors the album, is most emblematic of Da Real World’s political ambitions. At the time, “bitch” was still a mostly derogatory term aimed at women, or men who were lacking; Missy wore it like a diamond-encrusted brooch. A bitch became a woman who knew herself, and knew what she was owed. —Peters
What makes this album so good? The Roots’ fourth album arrived at what Questlove later called the group’s “do-or-die moment.” Spoiler: They didn’t die, they went platinum. What changed? In the late ’90s the Roots found perfect collaborators in the Soulquarians, a collective of vibe-heavy artists who accentuated each other’s strengths. So there was D’Angelo on the keys, Erykah Badu on a hook, J Dilla on a beat, and verses from Common, Mos Def, and a then-unknown Beanie Sigel. It was jam-band gold, and fertile ground for expansion: Things Fall Apart kicked off a sterling Soulquarians run that later included D’Angelo’s Voodoo and Badu’s Mama’s Gun.
What is the key song on this album, and why? “You Got Me” received all the plaudits (and a Grammy), but “The Next Movement” always stood out to me as the platonic ideal of a Roots song: a stirring showcase of live instrumentation, hip-hop fundamentals (scratches by DJ Jazzy Jeff!), and—always—Black Thought’s peerless delivery.—Kwak
What makes this album so good? If an artist as sui generis as Bill Callahan can have a gateway drug, Knock Knock is it. After nearly a decade of oblique, scratched-out noise, there is something plaintive, almost foot-stomping, about this album. “Let’s Move to the Country,” he sings on the first song, as direct a statement as he’d ever make. This is the blueprint for the edifice he’d go on to build for the next 20 years—iron-lunged troubadour anthems, sung with a straight face and a stiff back.
How does this album serve as a defining moment for music in 1999? Well, the album’s best song is called “Cold Blooded Old Times”—the kind that “turn your bones to glass”—and if you couldn’t see the agony that lay ahead, you weren’t paying attention. —Fennessey
What makes this album so good? It’s a Beach Boys record, played by a Cars cover band, full of songs that sound like the perfect day but are actually about life falling apart all around you. Heartbreak and addiction run through the album, juxtaposed with ecstatic moments of power-pop. Wedged in between two acknowledged masterpieces in the Wilco discography—1996’s Being There and 2002’s Yankee Hotel Foxtrot—Summerteeth is somewhat overlooked. It didn’t signal a breakout, or respond to a moment in the national consciousness like those other two albums did. But, song for song, it might be the band’s strongest full-length, and we’re talking Wilco, so that’s no small feat.
What is the key song on this album, and why? Let’s talk about “ELT.” I think it took me a solid … three-dozen listens to figure out how desperately sad this song was. Summerteeth was infamously stitched together by Wilco frontman Jeff Tweedy and his then-musical wingman Jay Bennett (Bennett would pass away in 2009), but “ELT” sounds like Wilco snatching the title of the next Tom Petty and the Heartbreakers. It might be studio magic, but here is the best bar band in the world, combining all of Wilco’s best traits: an easy fluency between roots rock, new wave, and symphonic pop. It sounds like hitting the PCH at sunset with no traffic, but it’s about the opposite of that: isolation, loneliness, and loss. —Ryan
What makes this album so good? The Hot Rock is Sleater-Kinney’s least straightforward and most inwardly focused record. A departure from the righteous punk fury of their breakthrough 1997 album Dig Me Out, these intricately composed songs play out like extended conversations between the interlocking riffs and complementary vocals of Carrie Brownstein and Corin Tucker. (The Hot Rock is also the most persuasive musical argument that Sleater-Kinney didn’t need a bassist, especially when you’ve got a rhythm section as formidable as drummer Janet Weiss.) Knotty, moody, and profoundly impassioned, The Hot Rock’s complexity gives it an enduring staying power.
What is the key song on this album? The poetic, overcast “Get Up,” a vivid evocation of feeling stuck that turns into a hard-won ode to carrying on. And its stirring music video, directed by Miranda July, is an indie classic in its own right. —Zoladz
What is the key song on this album, and why? “The Plan.” The first song from the band’s fourth album circles the square. BTS’ dueling styles—anthemic, “Cortez the Killer”–guitar gout and aw-shucks Midwestern indie pop—come together with grounded grandeur. This is the song you play after scoring the winning touchdown at the homecoming football game, or after fumbling on the 1-yard line.
How does this album serve as a defining moment for music in 1999? Consider it a last gasp of sorts, as major labels began shifting away from mining indie acts in the aftermath of grunge’s reign. The Strokes, the White Stripes, and Interpol would soon come to represent a new rock vanguard. But in ’99, Blur and Beck and the Beta Band continued to crest on a wave of Buzz Bin beneficence, and Keep It Like a Secret stood like a totem—10 feet high, and a little wide. —Fennessey
What makes this album so good? In an era when rap albums were increasingly becoming blockbuster events, Dr. Dre’s comeback album was the biggest of them all. (Seriously, it opens with the THX sound effect.) Fresh off giving suburban America its next great scare, Dre returned to the studio with a cadre of coproducers and emcees and built the most decadent party album of the late ’90s. Minus the rampant misogyny, 2001 sounds as fresh today as it did back then: Dre had never rapped better (though he had some help) and his beats had never thumped harder.
How does this album serve as a defining moment for music in 1999? Aside from reestablishing Dre the solo artist as a commercial concern, the album was a victory lap for Eminem, and an unofficial coming-out party for the Shady-Aftermath alliance that would rule over the early 2000s (thanks in part to one key addition, of course). —Sayles
What makes this album so good? The Dismemberment Plan of Emergency & I was the same D.C. band behind 1995’s ! and ’97’s The Dismemberment Plan Is Terrified, but the album was different. The production, sound, and syncopation was tighter, the arrangements more precise in their idiosyncrasies. Each track told its own story—the discordant, confrontational opening of the anthemic “What Do You Want Me to Say”; the 15/8 time signature of “Gyroscope”; the closing “Back and Forth,” a kiss-off to an earlier era—that, taken together, acted as a portal from the fuzzy, grungy rock of the 1990s to the electro-tinged, playful indie of the 2000s. They were a punk band with a synthesizer, math rock with an MC; they were the future.
What is the key song on this album, and why? I can’t say this about many songs, but I remember where I was when I first heard “Spider in the Snow.” My family had just moved across the country, and I was spending my first summer “home” from college in a city where I didn’t know a soul. Riding in the back of a coworker’s car, windows down, I heard its rising synth and bright guitar, then the bass and drums carrying Travis Morrison’s opening line, one of many that would stay with me and get me through whatever came next. The song isn’t the catchiest or most energetic on the record, but it is one of the most enduring. —Kjerstin Johnson
How does this album serve as a defining moment for music in 1999? FanMail—TLC’s epic follow-up to the diamond-selling sophomore album CrazySexyCool—was both of its time and blazingly ahead of it. Sure, on occasion it can sound like a Y2K-anxious relic of the dial-up era (see: the high-concept interludes spoken by an android named “Vic-E”), but in a larger sense it was one of the first pop records to take the internet seriously—and to understand how profoundly it would change the nature of connection, communication, and modern love itself.
What is the key song on this album? “No Scrubs” is the obvious answer, but don’t overlook the title track. “FanMail” is a glitchy symphony of digital noise, cut through with the very human longing of T-Boz’s sultry croon: “Just like you,” she sings, bemoaning the isolation of fame, “I get lonely too.” Does that all makes it sound like a proto-Drake song? Good—the 6 God himself has covered this song in tribute. —Zoladz
What makes this album so good? Its seamless diversity. The man now known as Yasiin Bey wasn’t the first rapper to explore genres beyond hip-hop, nor would he be the last. But very few artists have ever made as cohesive a project while combining so many elements: boom-bap, scat, spoken word, dancehall, soul, jazz—even punk. The Brooklyn native navigated every disparate sound on his solo debut with an effortless, electric verve. And make no mistake, this is a rap album. Rather than sounding disjointed, it is sequenced to perfection, a listening journey that rewards those who start at the beginning and don’t skip a stop.
How does this album serve as a defining moment for music in 1999? Mos Def and his Rawkus ilk were once heralded as the beacons of a burgeoning late-’90s indie scene. But the success of his solo debut made Mos less a counterpoint to commercial rap and more the point itself. He not only bridged the gap between underground and mainstream hip-hop but he also broke rap boundaries, paving the way for artists like Kanye West to comfortably do the same. —Kwak
From debutantes 50 Cent and Eminem to soon-to-be warring kings Nas and Jay-Z, these are the best rhymes of ’99—according to one NYC-centric hip-hop head named Donnie Kwak, anyway.
10. 50 Cent on “How to Rob” “I'll rob Pun without a gun, snatch his piece then run/This n*gga weigh four hundred pounds, how he gonna catch me, son?”
9. Eminem on “Forgot About Dre” by Dr. Dre “Chicka-chicka-chicka Slim Shady/Hotter than a set of twin babies/In a Mercedes Benz with the windows up/When the temp goes up to the mid-80s”
8. Witchdoctor on “Watch for the Hook” by Cool Breeze feat. Outkast & Goodie Mobb “Slithering/Making deals, delivering/Uh uh uh, that weed got you shivering”
7. Bun B on “Big Pimpin'” by Jay-Z feat. UGK “Go read a book, you illiterate son of a bitch/And step up your vocab”
6. Lil Kim on “Quiet Storm (Remix)” by Mobb Deep “I'm a leader, y'all on some followin' shit/Comin' in this game on some modeling shit/Bitches suck cock just to get to the top/I put a hundred percent in every line I drop”
5. Nas’s first verse on “Nas Is Like” “Freedom or jail, clips inserted, a baby's being born/Same time a man is murdered—the beginning and end”
4. Mos Def’s first verse on “Hip-Hop” “When your product in stock, the fair-weather friends flock/When your chart position drop, then the phone calls … /chill for a minute, let's see who else hot”
3. Jay-Z’s first verse on “So Ghetto” “I put your crew in hard bottoms/The priest is like, ‘God's got him. He never did nothin' to nobody but them boys shot him’”
2. Kurupt on “Xxplosive” by Dr. Dre feat. Hittman, Nate Dogg, & Six-Two “Bitch n*gga, you more of a bitch than a bitch”
1. Andre 3000 on “Da Art of Storytellin’ (Part 1)” “Talking ’bout what we gonna be when we grow up/I said, ‘What you wanna be?’ She said, ‘Alive’/It made me think for a minute, then looked in her eyes”
What makes this album so good? A portrait of the artists committing to the bit. Following up the critically adored Mutations, Beck circled back to the go-go-gadget, kitchen-sink funk of Odelay, and doused it in cheap cologne and stripper glitter, and gave it a Vegas light show. Turns out the revenge of the nerd feels a lot like a Tom Jones show on the Strip. With a palette of early electro-hip-hop, Bowie’s blue-eyed soul, and a heavy dose of Prince, Beck paints a mural of grotesque and funny and sincerely erotic sexuality. At the time, no one knew what to do with it: Was it cultural appropriation? Was it a joke? What happened to the troubadour from Mutations? Twenty years later, it sounds … like Beck. And it’s a great version of him.
How does this album serve as a defining moment for music in 1999? Beck rose out of the tape-trading, lo-fi indie scene of the mid-’90s, made a one-hit, and still managed to be an object of wonder. Midnite Vultures was the alternative rock icon grappling with, and fully indulging in, life as a full-blown pop star. He challenged the aw-shucks irony of his cohort, and at the same time gave the mainstream a truly subversive and absolutely head-knocking piece of music. —Ryan
How does this album serve as a defining moment for music in 1999? Clarity is the convergence between what emo was at the turn of the century and what it’d become in the decade that followed. It’s also a master class in how seemingly disparate elements—the hypnotizing slow build of “Table for Glasses” and the pounding opening notes of “Blister”; the radio-ready sensibilities of “Lucky Denver Mint” and the untethered bliss of “Goodbye Sky Harbor”—can come together to create something that’s astonishingly cohesive and complete. Jimmy Eat World’s landmark album beautifully captures the process of self-discovery, and all of the joy, despair, doubt, and hope experienced therein. It’s quintessentially 1999. It’s also timeless.
What is the key song on this album, and why? The three-song sequence from “Ten” to “Just Watch the Fireworks” to “For Me This Is Heaven” is not only the standout stretch of Jimmy Eat World’s third LP; it’s arguably the finest in the entire genre. The last of that trio perfectly distills why this album is a classic. In the wrong hands, a ballad like “FMTIH” could come across as sappy, or worse—disingenuous. In Jim Adkins’s, each lyric is disarmingly heartfelt and endearingly earnest. This song soundtracked thousands of rites of passage and inspired a generation of artists. Twenty years after its release, it’s just as affecting as ever. —Ben Glicksman
What makes this album so good? Shout-out to the title of this album—and my decades-late understanding of why my mom would not let me purchase it. Anyway, Enema is Blink-182 realizing their full capabilities, mixing punk and pop while tapping into the sense of life weariness growing among young people at the time, in ways both funny (“What’s My Age Again?”) and serious (“Adam’s Song”).
How does this album serve as a defining moment for music in 1999? Criticized as “not punk enough,” Enema of the State is something much more important: A bridge between the early pop-punk of Green Day and the Offspring and the 2000s pop-punk of Sum 41, Good Charlotte, and Fall Out Boy (and, uh, Green Day). —Gruttadaro
“It’s over / You don’t need to tell me,” moans Damon Albarn, over grimy, distorted, slightly twangy guitar, the ultimate sad alt rocker singing the ultimate sad-alt-rocker breakup song. “I hope you’re with someone who makes you feel safe when you’re sleeping tonight / I won’t kill myself trying to stay in your life / I got no distance left to run.” He is speaking, explicitly, to his also quite famous ex-girlfriend, Elastica leader Justine Frischmann, who is the quite unwilling inspiration for Blur’s sixth album, which Spin described at the time as “one long, petulant bender,” and which vacillates between startlingly gorgeous and startlingly weird. “No Distance Left to Run,” the record’s bravura closing power ballad, is one of the gorgeous parts.
Not content with merely being Britpop gods and Oasis archvillains, the fellas had at long last hit it big in America with 1997’s Blur, anchored by future hockey-arena staple “Song 2.” There is little woo-hoo’ing, however, on 13, a volatile and wounded monolith even at its noisiest (see “B.L.U.R.E.M.I.”), opening as it does with the incredible gospel-folk anthem “Tender,” a stomp-and-clap weep-along with a chorus that literally ends, “Love’s the greatest thing that we have / I’m waiting for that feeling / Waiting for that feeling / Waiting for that feeling to come.”
From there, things immediately get messier and brasher and goofier (see “Coffee & TV,” a silly earworm with a memorably weird guitar solo) under the watchful eye of producer William Orbit, who whips up a raucous psych-rock stew atypical of the guy who one year earlier had helped Madonna make Ray of Light. The cumulative effect is rowdy and staggering, and all the more so for the way it succeeds in musically documenting romantic failure. “He didn’t talk to me, he wrote about it,” Frischmann said of Albarn in a 2000 NME interview. “But if he’d spent as much time giving me emotional support as he spent writing songs about not getting it, we might not have broken up.” —Harvilla
Although 1998’s self-titled Destiny’s Child went platinum, it can’t compare to the success of The Writing’s on the Wall, which catapulted the group to genuine, ubiquitous superstardom. It’s also one of the best-selling R&B albums of all time, and signaled the then-foursome wrenching back some creative control from their label. Destiny’s Child was a little too En Vogue, and didn’t sound much like something 17-year-olds would be listening to or putting into the world of their own accord. Writing’s on the Wall is an inspired sophomore effort, bridging the pro-feminist R&B of the late ’90s (“Say My Name”) and the power pop of the early aughts (“Jumpin, Jumpin”). What resulted was a chart-gripping juggernaut and duly, what popular music would sound like for a decade. —Peters
It was hard to check your mentions in the late ’90s, but while touring in support of her breakthrough 1996 debut album Tidal, Fiona Apple got the chance. She was flipping through Spin, an issue that happened to be the one after she’d been on the cover, so she was confronted with some unflattering letters to the editor about herself: “She’s the most annoying thing in the world,” etc. She got upset. She cried a little. And then she did the most Fiona Apple thing imaginable: She picked up a pen and wrote a defiant 90-word poem that she ended up liking so much that she decided to use it as her next album title. Ninety words is short, for a poem. For an album title, it was then the longest in history. When the Pawn... garnered Apple a gold record and a Guinness World Record plaque.
Fiona Apple does nothing in half measures. She makes art out of excess, spillover, and has always seemed emboldened by the accusation—all too familiar to a lot of women—that she is somehow too much. At the same time, her magnificent, Jon Brion–produced sophomore album shows restraint in all the right places. Maybe it’s just maturity: Tidal introduced her as a precocious teenage powerhouse, but its verbose lyrics occasionally suggested that she hadn’t yet grown into her thoughts. When the Pawn... is more lived-in, and more direct. “When I think of it, my fingers turn to fists,” she sings on “Limp,” banging on the keys until her piano becomes a percussion instrument. She’s developed a wry self-awareness, too, as evidenced by the jazzy, Ella Fitzgerald–esque “Paper Bag.” “I went crazy again today,” she shrugs. Print that in a letter to the editor.
The dedication takes up an entire flap of the CD’s fold-out booklet: “for pta.” Apple wrote most of this record while she was dating another arty ’90s wunderkind with big ideas, Paul Thomas Anderson, and he directed all the When the Pawn… videos (including the frenetic Laurie Anderson homage “Fast As You Can”). Both would go on to struggle against respective industries that could barely contain their outsize talents, though Apple would have a much tougher time securing the artistic freedom she seems to have now. Still, When the Pawn... remains a quintessential artifact of the end of the century, a wildly uncompromising sophomore record, a fiery, poetic fuck-you to anyone who asked Fiona Apple to play by the rules. As long as this world remains bullshit, When the Pawn... will be a salve. —Zoladz
In 2013, Jay-Z ranked Vol. 3 third-to-last in his catalog, which at the time totaled 12 albums. Why was he so uncharitable toward his fourth album, which most of his diehard fans love? Is it because his repertoire is that loaded? Or maybe we can’t trust him to critique his own work? (He slotted that year’s Magna Carta Holy Grail four spots higher. With all due respect, Hov: FOH!) Here’s my guess: Vol. 3’s highs (“So Ghetto,” “Big Pimpin’”) are among Jay’s very best, but its lows are among his absolute worst. He probably wants you to forget he ever recorded “Things That U Do,” “S. Carter,” and “Pop 4 Roc,” a trio of songs that aged like an open can of Dr Pepper. The less said about them, the better.
It’s best to remember Vol. 3 not for a particular song (though “Snoopy Track” remains underrated) or a verse (the opening 16 on “Come and Get Me” is unfuckwittable) or a beat (Irv Gotti produced “Watch Me,” never forget), but instead for the fact that the album represents Jay-Z’s first decree as hip-hop’s new king. He would prove to be a ruthless ruler. No rapping upstart (looking at you, Gillie and 50), love interest (“First time they fuss I’m breezin’”), neighborhood snake (“Trust me, I’m still street”), or alleged bootlegger (sorry, Un) was going to challenge his crown. And none did (until he met Beyoncé).
Vol. 3 is far from cohesive, possibly by design: Jay-Z wanted to show that he could excel on any kind of track—even a shitty one—using any kind of flow. He succeeded. It’s definitely not his best album, on that Jay and I agree. But I’d argue Vol. 3 is the album when Jay-Z was rhyming the best. —Kwak
Rage Against the Machine’s The Battle of Los Angeles is a chiaroscuro of false alarms and furious injustice, maybe the noisiest, most punishing album to go (double) platinum in America. Rage was always a conundrum—promoted and supported by major label Sony, but warring with the structural integrity of wealth and power in every warped lick it unloaded on its audience. This album, their last of original compositions, is a complex concept—unfailingly righteous and downright steaming with anger. But it’s also, like the best Rage, strangely catchy. The band was led by guitarist godhead Tom Morello, a futurist technician in a ball cap, and MC Zack de la Rocha, a man who found ways to make slam poetry earnestness and campus activist intensity seem tuneful. Together they wrote songs to create awareness about the imprisoned journalist Mumia Abu-Jamal, the teachings of Chinese Communist leader Mao Zedong, the dark heart of American colonialism, and especially about the Zapatistas and the Mexican struggle in that country and at home.
This album is the band’s masterwork—but not because it has aged gracefully, necessarily. It sliced through the era’s politbureau rabble and Clintonian smoothness simply by screaming at the top of its lungs. But its prescience and full-throated commitment to its ideas never comes at the expense of a song you want to listen to. This has always been a difficult proposition in American pop music, from the soft-footed hippie folk that protested the war to Public Enemy’s haunted, frantic panic in the streets. At what cost a song? The compromise has felled many artists in recent history. Rage needn’t worry; the band knew a lot. They seemed to have a song for every oncoming tragedy. The Iraq War? “War Within a Breath.” The financial meltdown of 2008? “Sleep Now in the Fire.” The subprime housing crisis? “New Millennium Homes.” The immigration nightmare of 2019? “Maria.” The amusing-ourselves-to-death chokehold of the 21st century? “Testify.”
The movie ran through me
The glamour subdue me
The tabloid untie me
I'm empty please fill me
This isn’t a fun album to think about, and many of the band’s contemporaneous fans didn’t think about it at all. They just thrashed along to its brute-strength riffs and de la Rocha’s berserker wail. I did, sometimes. Rage could sit comfortably on a bill with Limp Bizkit and Korn, and sometimes did just that. But they shared virtually nothing. The package said “rock” or “metal” or “rap.” But what it contained was something far more serious, and far more dangerous. It’s still explosive. —Fennessey