The Year: 1999

Billboard Hot 100’s Top 20 Songs Of 1999

1. Cher, “Believe”

2. TLC, “No Scrubs”

3. Monica, “Angel Of Mine”

4. Whitney Houston feat. Faith Evans and Kelly Price, “Heartbreak Hotel”

5. Britney Spears, “…Baby One More Time”

6. Sixpence None The Richer, “Kiss Me”

7. Christina Aguilera, “Genie In A Bottle”

8. Sugar Ray, “Every Morning”

9. Deborah Cox, “Nobody’s Supposed To Be Here”

10. Ricky Martin, “Livin’ La Vida Loca”

11. 702, “Where My Girls At”

12. Jennifer Lopez, “If You Had My Love”

13. Goo Goo Dolls, “Slide”

14. Brandy, “Have You Ever?”

15. Backstreet Boys, “I Want It That Way”

16. R. Kelly and Celine Dion, “I’m Your Angel”

17. Smash Mouth, “All Star”

18. Sarah McLachlan, “Angel”

19. Santana feat. Rob Thomas, “Smooth”

20. TLC, “Unpretty”


It was 1999, and we were preoccupied with the future. In the year of Y2K panic, one of the biggest movies in theaters depicted a digital dystopia powered by blissfully unaware human batteries, the kung-fu choreography, bondage-pants aesthetic, and surveillance imagery of which must’ve been in the air at the time, because they’re all over the inescapable clip for the year’s No. 2 single. (In all fairness to the Wachowskis, theres’s a lot of Besson and Barbarella in the “No Scrubs” video, too.) The 1999 hit parade marched to the beat of youth, as squeaky-clean pop stars with Disney pedigrees paired with Swedish songwriting scientists to beguile listeners with undeniable melodies and lyrics that raised more questions than they answered. The Backstreet Boys never wanted to hear you say, “I want it that way” (Which way? And what “it”?), on an album titled, aptly, Millennium.

It was 1999, and we couldn’t stop thinking about the past. Backstreet Boys, ’N Sync, and 98 Degrees set the stage for solo-act comeback plays from former New Kids On The Block Jordan Knight and Joey McIntyre, while Menudo graduate Ricky Martin capitalized on the Latin explosion that boosted the musical profiles of one-time Fly Girl Jennifer Lopez, Enrique “Song Of Julio” Iglesias, and Woodstock survivor Carlos Santana. There was another Woodstock, albeit a 30th-anniversary edition whose mark on the cultural consciousness was one of flames, violence, and assault. MTV’s cameras were there to capture it all, live; five months later, as the channel counted down to 2000 in its Time Square studio (and a precious few still wondered if all computerized systems would fail at midnight), No Doubt prepared to ring in the New Year with a cover of R.E.M.’s “It’s The End Of The World As We Know It (And I Feel Fine).” That studio hosted daily fights for chart supremacy between teenyboppers, nü-metal sulkers, pop-punk pranksters, and one white MC from Detroit with a thing for potty humor and revenge fantasies. But as Gwen Stefani rattled off Michael Stipe’s 12-year-old free associations, Billboard’s year-end list was topped by 53-year-old pop survivor Cher.

It was 1999, and we were still pretty hung up on 1998. So many of the musical milestones associated with the second-to-last year of the 20th century were a hangover from the previous 365 days: The aforementioned MTV battleground, Total Request Live, was back-to-school programming for the ’98-’99 academic calendar. “Believe”—the dance-pop number that ushered Auto-Tune into the mainstream and gave Cher her fourth-consecutive decade with a top 10 hit—came to radio and clubs the same fall. Lauryn Hill’s record-setting night at the Grammys in February of 1999 was secured by an album that was released the previous August—though “Doo Wop (That Thing)” had enough steam to wind up in the middle of Billboard’s class of 1999, one spot above “Mambo No. 5.”


Even amid a grand experiment in nostalgia like The A.V. Club’s 1999 Week, it’s hard not to lose yourself in marveling at the historical sweep of one year in popular music. But ’99 also gave us unique time capsules like the left-field success of “Steal My Sunshine”—a beachy pop sensation by an alt-rock band from Canada—or the bowdlerized Cash Money smash “Back That Thang Up.” (And let’s not forget about the meme-making double header of “Smooth” and “All Star.”) Gigantic acts of the time like TLC and Whitney Houston occupied prime spots in an almost-entirely women-owned top 10, but a lot of the year’s musical superstars were ascendant: No. 5 act Britney Spears and her fellow former Mouseketeer at No. 7, Christina Aguilera, for example. Destiny’s Child made its first dent in the charts that year with “Bills, Bills, Bills”; the future Mr. Beyoncé Knowles, JAY-Z, flexed his mogul acumen with a diversified portfolio that included a new album, a soundtrack hit, a signature track whose hook set the blueprint for The Blueprint, and a verse on Mariah Carey’s last great pre-Glitter jam.

At the dawn of the decade when “poptimism” made its way into the critical discourse, 1999 made a strong argument that top 40 could be taken just as seriously as more underground sounds with canonical smashes like “No Scrubs,” “…Baby One More Time,” and “Hard Knock Life (Ghetto Anthem).” But, as with any year in the modern pop era, that’s only part of the story. It was 1999, and it was a fertile time for “alternative” strains of traditionally populist genres like hip-hop and country. It was 1999, and a British electronic act was, like Douglas Adams before them, warning us to “Don’t panic.” It was 1999, and the punks were dancing, feeling, twisting themselves into abstract shapes. It was 1999, and this is what it sounded like.

Smog, “Cold Blooded Old Times” (January 12)

Like Drag City labelmate Will Oldham, Smog’s Bill Callahan can be difficult to pin down, his lyrics at once familiar and elusive, bare and oblique. “Cold Blooded Old Times,” off of 1999’s Knock Knock and appearing on the High Fidelity soundtrack a year later, encapsulates a certain Smog haziness. There are only flashes of scene here—a broken gate, children witnessing far too much—but as with the “type of memories that turn your bones to glass,” sometimes a glimpse is all it takes; however poorly one might remember a trauma, its dark significance remains. The song’s themes of family secrets run counter to its hand claps and chugging rhythm, the music insisting, like the speaker’s mother, that everything is fine, though it most certainly isn’t. With lyrics as indelible as Callahan’s own impossibly deep voice, and a fuller sound than in the singer-songwriter’s previous, lo-fi experimentations, Knock Knock would mark a turning point in a career that only continues to evolve. [Laura Adamczyk]


Bonnie “Prince” Billy, “I See A Darkness” (January 19)

Perhaps the most well-known song in Will Oldham’s extensive catalog, “I See A Darkness” came to prominence not when it was released, but a year later, when Johnny Cash included a cover version on 2000’s American III: Solitary Man (with Oldham singing backup); elegiac and laden, Cash’s is a song about dying sung by an ailing man. But the original, from Oldham’s first album under the Bonnie “Prince” Billy moniker, is something else. Here the darkness is not death but a spiritual lead blanket, a midnight of the soul. Glacially slow, it sounds like it’s meant to be absorbed through the skin rather than listened to. Twelve years after his collaboration with Cash, Oldham would re-imagine the song yet again—in a jaunty rendition with Angel Olsen providing backup vocals. Oldham has long been a shifting sort, a musician who would argue that a song changes each time it’s sung, persona and performance as important as the music itself. Whether or not the original is the best version is perhaps not the right question to ask, but in 1999, it laid the foundation for its few yet significant reimaginings. [Laura Adamczyk]

Built To Spill, “You Were Right” (February 2)

“You Were Right” is not the best song off of Built To Spill’s breakout Keep It Like A Secret (that would be, in my mind, “Carry The Zero”), but it’s perhaps the most original, for the way it toys with the very idea of originality. Part sincere, part tongue-in-cheek, Doug Martsch patchworks “You Were Right” out of lyrics from other songs, but not just any lyrics—only the most famous, most clichéd lines from classic rock’s greatest, or worst, hits, depending on who you ask. From The Rolling Stones to The Doors, it’s song as collage, using something old to make something new, while nevertheless remaining very Built To Spill: with its wailing guitars from frontman Martsch, who plays the instrument as though he were choking it, and drums that put a period at the end of every sentence. Each era’s artists work to distinguish themselves from those of the past, but “You Were Right” makes plain just how much Built To Spill was influenced by its forebears, while simultaneously poking fun of them. It’s as if to say that a rock song doesn’t need to have great lyrics in order to be good; sometimes it’s better if it doesn’t. [Laura Adamczyk]


The shards of Jason Molina’s shattered heart are sharp enough to draw blood on Axxess & Ace, Molina’s third album under the Songs: Ohia name. Arranged and recorded live in-studio, and backed by a crew of Chicago indie all-stars, Axxess & Ace has an emotionally risky spontaneity about it, the all-or-nothing urgency of telling someone how you really feel. Songs: Ohia’s music is often crushingly depressing. But Molina’s signature tangle of messy emotion spins into a seductive waltz on the album’s centerpiece, the nearly-eight-minute long “Captain Badass.” Opening with a sexy flick of brushes across a snare drum and culminating with Molina belting, “You don’t have to think twice, if it’s love you will know,” the song captures the choking anxiety of questionably requited love (and lust). Combined with the rawness of its arrangement, this vulnerability makes “Captain Badass” the perfect song to scream along to with the windows rolled down, driving home alone on a hot summer’s night. [Katie Rife]

Scottish rock outfit Mogwai would’ve been just fine had it doubled down on the thundering catharsis of its studio debut, 1997’s Mogwai Young Team. But by subverting expectations with 1999’s softer, more thoughtful Come On Die Young, Mogwai shook off the Slint comparisons that dogged the band, while demonstrating a sensitivity and creative confidence that distinguished it in the post-rock space. “It’s the difference between how fast you ride your bike and how slow you ride it,” frontman Stuart Braithwaite told The Sunday Herald, addressing the differences between Young Team and its follow-up. “It’s always harder to ride your bike slow.” Songs don’t get much slower than “Cody,” an aching, overcast track that unfolds across six and a half minutes of lonely lap steel and cymbal wash. It’s the only cut on either of Mogwai’s first two albums to prominently feature vocals, but not the last. With the likes of Rock Action, Mr Beast, and its myriad soundtracks, the band’s approach to the human voice has continued to evolve along with its sound. It’s why we still talk about Mogwai today. [Randall Colburn]

Basement Jaxx, “Red Alert” (April 19)

Released in April 1999, house banger “Red Alert” introduced the world to both the music and mentality of British club heroes Basement Jaxx. Deeply dance-friendly and practically made for drugged-out nights chugging along on a dance floor, the debut single made bigger waves in the U.K. than it did in the U.S., though it did catch the attention of Stateside writers like The A.V. Club’s Joshua Klein who noted that the track “has more than enough faux funk and chic camp to keep the masses moving.” The track has since been licensed everywhere from Bend It Like Beckham to Coca-Cola commercials, making it one of the most commercially successful non-charting cuts of the year. [Marah Eakin]


Old 97’s, “Murder (Or A Heart Attack)” (April 27)

Forming slightly after Uncle Tupelo, but before bands like Whiskeytown and Drive-By Truckers, the Dallas-birthed, Rhett Miller-fronted Old 97’s are considered to be among the forefathers of alt-country. The group is still together today, and has found fairly lasting success on the road, but its commercial peak came with 1999’s “Murder (Or A Heart Attack),” off of Fight Songs, one of the band’s best records. Although it’s definitely more pop than twang, “Murder (Or A Heart Attack)” still blends loss, love, and pathos—though in this case, the lost love is Miller’s roommate’s cat, who slipped out of the window of their shared apartment. The cat was found safe and sound, but in true alt-country fashion, Miller still managed to get a kick-ass song out of the whole affair. [Marah Eakin]

Blackalicious, “A To G” (April 30)

Emerging in the early ’90s on the heels of acts like De La Soul, The Pharcyde, and A Tribe Called Quest, alternative hip-hop had been commercially silenced by the late ’90s—due in part mostly to the emergence of gangsta rap and then (shudder) rap rock. Still, its message and sounds bubbled under the surface in places like the Bay Area, where acts like DJ Shadow, Lateef The Truthspeaker, and Lyrics Born were all plugging away at their music. This same scene birthed the insanely talented Gift Of Gab and Chief Xcel, who came together in the early ’90s to form Blackalicious. With 1999’s A2G EP, the pair found minor commercial success, making a small wave on the U.K. label charts. The standout single—which would also appear on the group’s 2000 full-length, Nia—is Gift Of Gab’s tongue-twisting “A To G,” which finds the rapper weaving his way through the alphabet line by line, creating a rap that’s both technically amazing and pretty damn catchy. [Marah Eakin]

Sigur Rós, “Starálfur” (June 12)


All clichés are rooted in truth, but calling “Svefn-g-englar” “cinematic” is the cliché that became truth: The second track on Sigur Rós’s second album has always called out for a movie or TV to draw on its sense of the epic. There just wasn’t anyone to pick up the call until Ágætis byrjun’s Stateside release in 2001, at which point Hollywood—beginning with Cameron Crowe and Vanilla Sky—was perpetually on the line. The 10-minute track sure provides enough points of inspiration: the opening drones, the wordier middle passages, that spot around the sixth minute where Ágúst Ævar Gunnarsson’s snare fills marshal an impression of Radiohead covering Dark Side Of The Moon. In the roar of his bowed guitar, Jónsi Birgisson conjures an ambient soundscape of glacial endlessness, the lullaby-like reassurance of his voice preventing it all from getting too overwhelming. [Erik Adams]

Ali Farka Touré, “Ali’s Here” (June 22)

Late Malian musical legend Ali Farka Touré once said, “I play traditional music and I don’t know what blues is,” which makes the similarities between his hypnotic guitar playing and that of American bluesmen, particularly John Lee Hooker, all the more fascinating. A student of Malian music, Touré switched to a Western-style guitar after hearing it played by Guinean musician Fodéba Keïta; by the time 1999 rolled around, he had risen from cult fame to become an internationally famous Grammy winner, and rejected it all to move to a farm near the village of Niafunké back home in Mali. That village became the name of his last album, before he (mostly) retired in 2000. Touré says in the CD pamphlet, “This record is more real, more authentic… My music is about where I come from and our way of life and it is full of important messages for Africans.” Even for outsiders, it’s possible to appreciate a song like album opener “Ali’s Here” simply for the virtuosic mastery and psychedelic complexity of the music itself. [Katie Rife]

Guided By Voices, “Teenage FBI” (August 3)

Ever restless and suspicious of its own popularity, Guided By Voices responded to the accolades for its mid-’90s run of lo-fi masterpieces by… signing with a major label? Although, in comfortingly underachieving fashion, the record was delayed long enough that the band’s deal with Capitol Records fell through, the polished new sound producer Ric Ocasek fashioned on Do The Collapse was nevertheless considered a betrayal by GBV’s more purity-obsessed fans. That’s their problem, though, as with the benefit of hindsight the classic-rock influenced, radio-friendly guitar sound on Do The Collapse goes with Robert Pollard’s idiosyncratic songwriting like a sprinkle of chili powder on a bowl of fresh fruit. Witness “Teenage FBI,” the euphoric album opener that could have been GBV’s breakthrough hit, had eventual label TVT picked it as the lead single rather than the anemic “Hold On Hope.” It’s one of GBV’s all-time catchiest melodies, blended with the angst that seeps through the group’s signature eccentricity in Pollard’s best lyrics. And that avalanche of fuzz that overwhelms the chorus? It’s a better buzz than shotgunning a six-pack of beer. [Katie Rife]


The Magnetic Fields, “The Luckiest Guy On The Lower East Side” (September 7)

69 Love Songs is Stephin Merritt’s White Album, a sprawling three-hour triple CD that flows from stream-of-consciousness goofs to delicate nuggets of melody as elegant as anything ever composed by Messrs. Lennon and McCartney. “The Luckiest Guy On The Lower East Side,” a knowingly self-deprecating little ditty accompanied by whimsical ukulele and set to a squishy synthesizer beat, is a combination of the two. The song’s melody is undeniably sweet, but the underlying nice-guy sentiment is vaguely unnerving; similarly, its odd instrumentation is as novel as the concept—taking a pretty girl for a ride in your car—is classic. 69 Love Songs is less a collection of love songs than a concept album about love songs, and critics on the cusp of the irony-drenched ’00s went absolutely bugshit for it. A Pitchfork 9.0 doesn’t necessarily equate to record sales, however—though Merritt’s small-but-devoted cult presumably didn’t mind keeping this one to themselves. [Katie Rife]

American Football, “Never Meant” (September 14)

The opening song on American Football, “Never Meant” is an undisputed emo classic, to the point where the song—and the album cover—have both been meme’d into oblivion. Even if it makes for some pretty solid jokes, there’s still a reverence for “Never Meant” that runs through the modern emo community. Because, while it’s easy to poke fun at, it’s also the kind of song that’s impossible to replicate. While detractors would call it melodramatic, there’s something comforting in the way Mike Kinsella sings of his broken-hearted regret, never sounding spiteful, but instead idealistic, as he wishes for everyone to just forget that the whole ordeal of a relationship ever happened. Built on math-rock riffs and a jazz-influenced backbeat, “Never Meant” remains the yardstick that all emo songs are measured against, because while it’s a perfect encapsulation of messy, teenage feelings, it still feels resonant and applicable when you enter adulthood. [David Anthony]

The Get Up Kids, “Holiday” (September 21)


The story of The Get Up Kids’ sophomore LP, Something To Write Home About, is one of chances taken and rewarded: adding keyboardist James Dewees to the lineup, recording on the West Coast rather than in the band’s native Midwest, signing with Vagrant Records, Vagrant literally betting the house on the record. The string-scrape fanfare that kicks off Something To Write Home About is the first indication of a payoff, swiftly confirmed by the rest of the album’s propulsive lead track, “Holiday.” The whirring synths beneath Matty Pryor and Jim Suptic’s fret-ascending gallop bring a new density to the fusion of pop-punk melody and heart-on-sleeve sentiment that was bubbling up from the underground thanks to The Get Up Kids and contemporaries like The Promise Ring and Jimmy Eat World. Jimmy Eat World took its own big chance in 1999 with its majestic Capitol Records swan song Clarity, but tracks like “Holiday” meant that emo’s crossover hopes wouldn’t fade out with “Goodbye Sky Harbor.” It also put The Get Up Kids on the cutting edge of refusing the “emo” label, but Something To Write Home About is nothing if not emo. There’s no ignoring the fact that the album begins with an anthem about feeling alone, betrayed, and unfamiliar with your surroundings, one that was most satisfying when it was screamed along to with dozens of dorks in chunky frames and thrift-store T’s who were soon swearing allegiance to the entire Vagrant roster. [Erik Adams]

MF Doom, “Rhymes Like Dimes” (September 22)

On the one hand, Daniel Dumile defied the “look at me” ethos of late-’90s commercial hip-hop by donning a mask for Operation Doomsday, his debut album under his most famous moniker, the comic book-inspired MF Doom. (Other Dumile pseudonyms: King Geedorah, Viktor Vaughn, and Metal Fingers.) But while his vengeful, deformed MF Doom persona came from a personal, painful place—Dumile’s younger brother and bandmate DJ Subroc was killed by a motorist in 1993, and their group KMD’s second album, Black Bastards, was buried by its label shortly afterwards—he’s still full of braggadocio about his mic skills on “Rhymes Like Dimes.” Built around an undeniably cheesy Quincy Jones sample, the song is a great example of MF Doom’s unique flow, which pulls in fleeting, free-form thoughts and shapes them into solid gold bars full of complex rhymes and nuanced rhythms. That idiosyncratic style has since become a cornerstone influence on independent hip-hop artists like Earl Sweatshirt and Tyler, The Creator, both of whom freaked the fuck out upon meeting Doom at a festival back in 2013. Besides, how can you not smile when DJ Cucumber Slice exclaims, “Buttery… biscuits!?” [Katie Rife]

The Dillinger Escape Plan, “43% Burnt” (September 28)



If mathcore, that particularly technical and complex subspecies of hardcore punk, has its own Paranoid—its own watershed masterpiece, inspiring a thousand offspring—it’s probably Calculating Infinity. And if the debut album by The Dillinger Escape Plan has a clear standout, it’s the mind-bogglingly berserk “43% Burnt,” which epitomizes this seminal, now defunct band’s chaotic plan of attack, marrying one-time vocalist Dimitri Minakakis’ roaring intensity to a polyrhythmic pile-up of instrumentation. The song even has a hook, of sorts: the stuttering riff that opens and closes the song, guaranteed to ignite any pit at note one. [A.A. Dowd]


Handsome Boy Modeling School, “Rock N’ Roll (Could Never Hip Hop Like This)” (October 19)



“Ladies and gentlemen!” Rap at the end of the millennium may have been dominated in mainstream pop culture by The Slim Shady LP and The Chronic 2001, but in college parties across America, an alternative boom bap was emanating from speakers, and it possessed a very different spirit. Thanks to Prince Paul and Dan The Automator, Handsome Boy Modeling School—a project named after a joke from an episode of the cult Chris Elliott TV show Get A Life—became one of the biggest success stories of the year. And its statement of arrival was “Rock N’ Roll,” a blast of purely celebratory bass-thump, heralded with horns, keys, and one of the funkiest beats imaginable. Kicking off the record, the track possesses none of the clever, nerdy rapping found in the subsequent tracks, just a dance-floor-ready rhythm and sense of infectious joyous abandon. Sure, it was the year of Black On Both Sides, Things Fall Apart, and other serious-as-a-heart-attack classics, but none of them had the sense to feature a track of Chris Elliott muttering, “Modeling just sucks!” over and over, now did they? [Alex McLevy]

The Dismemberment Plan, “You Are Invited” (October 26)

Emergency & I was the Dismemberment Plan’s first album on Interscope, and the move to a major label shows in the album’s more polished, but still aggressive sound. “What Do You Want Me To Say?” is a maelstrom of frustration, Travis Morrison’s talk-singing (given his obsession with hip-hop, you might even call it rapping) on the verses leading to a chorus that’s just melodic shouting of the exasperated title. But The Dismemberment Plan had never been more expressive than on Emergency & I—previous releases ! and The Dismemberment Plan Is Terrified had plenty of bluster, cementing the band’s position as dance-punk pioneers. “You Are Invited” veered furthest from the snottier sound of those early albums, laying out a new and promising path for the band. The song tells a story about isolation that it aims to resolve. Beginning with an impartial tone and almost diffident keys, the track explodes into a joyous chorus that dispels any sense of alienation, one loud and boisterous enough to reach even the most disaffected of youth. [Danette Chavez]

Le Tigre, “Deceptacon” (October 26)


At decade’s end (and after starting her own musical rebellion), Bikini Kill frontwoman Kathleen Hanna set punk dancing toward a new millennium—by way of what one future Le Tigre remixer would dub “the unremembered ’80s”—with a three-minute burst of sampler scrambling and scene commentary named for the bad guys from Transformers. The metamorphosis demonstrated by “Deceptacon” wasn’t as drastic as a jet fighter turning into a villainous robot, but the beats and the synths did represent new sonic settings for Hanna’s razor-sharp rejoinders to rock ’n’ roll condescension and bad sex. Explicitly feminist and queer, Le Tigre pointed toward all the Karen Os, Beth Dittos, and Peacheses to come, but “Deceptacon” knows its history, too: This song is the future The B-52s wanted, with a riff straight from the Ricky Wilson “stupidest guitar line you’ve ever heard” school. We may never know who took the “bomp” from the “bomp alomp alomp,” but “Deceptacon” sure rams some rama-lama ding dongs. [Erik Adams]

The Faint, “Worked Up So Sexual” (November 1)

Although it wouldn’t reach its peak until a couple of years into the 21st century, electroclash was starting to simmer in 1999. Reveling in a blend of new wave, synth-pop, and electronica, electroclash acts had a sense of humor about themselves that most bleeps-and-bloops acts lacked, as well as a flair for the darkly dramatic. All of that is evident in “Worked Up So Sexual,” the third song off The Faint’s 1999 breakthrough Blank-Wave Arcade. Starting with electro-squiggles and ultimately building into a chorus of clanking cranks and in-out rhythms, “Worked Up So Sexual” is a look at the ethics of sex work, but set to a club-friendly beat. It’s the perfect introduction to what The Faint would go on to perfect on albums like 2001’s Danse Macabre. [Marah Eakin]

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