99 Best Songs of 1999: Ranked by Rob Sheffield – Rolling Stone
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Rob Sheffield’s 99 Best Songs of 1999

Timeless classics and shameless one-hit wonders from a year when nothing made any damn sense (in the best possible way)

tlc britney blink 182 99 of 1999

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Man, it was a hot one. 1999 was the year music exploded, the year when nothing made any damn sense, the year fans had to throw out any old-school rules for how pop worked. The radio was suddenly full of shiny new stars. So many timeless classics. So many shameless one-hit wonders. So much crazed innovation, all around the margins. Teen-pop happened. Nu-metal happened. Every genre was booming. Let’s put it this way: If you spend an hour at your local karaoke bar, you’re going to hear somebody belt at least one hit from the summer of ’99. It was one of those pop moments when all that glitters actually is gold.

So let’s break it down: the 99 best songs of 1999, 20 years later. The hits, the flops, the flukes, the obscurities. Whatever type of music you loved, this year had it: hip-hop, electronica, indie rock, punk garage, country, R&B, disco sleaze. The old stylistic boundaries didn’t hold any more. “The walls came down,” as Sugar Ray’s Mark McGrath told me last year. “You would hear Kiss-FM or Z-100: ‘Coming right up, Mariah Carey, Blink-182, Eminem, Sugar Ray, and you’re like, ‘What the fuck is happening?”

Fans bought more music (with money! in stores!) than ever before or since. Nobody realized Napster was about to change everything. Carson Daly hosted Total Request Live on MTV every afternoon, where a new breed of stars got born: Britney, Xtina, Ricky, NSync, the Backstreet Boys. A previously unknown producer named Max Martin presided over the Orlandinavian connection that invaded the radio, in a strange alliance between the Swedes and the Mousketeers. Woodstock ’99 went down in flames. There was so much to hear, even great music could get lost in the rush — which is why going back means discovering new surprises. The world was cramming in as many pop thrills as possible before the Y2K crash. No rules. No shame. No scrubs.

There’s no way any list could sum up the year in a mere 99 songs — we could roll up to the thousands without running dry. As for what counts as a 1999 song, it’s all about the year of impact: Britney’s “Baby One More Time” technically dropped in late 1998, yet there’s no denying it belongs to 1999, when it conquered the world. On the other hand, Destiny’s Child’s “Say My Name” and Le Tigre’s “Deceptacon” came out on 1999 albums, but they spiritually belong to Y2K, when they went mega-nova. Cher’s “Believe” counts as a 1998 song — it was on last year’s list. (Though you could make a case it’s the song of the year, every year.)

Some of these songs turned into permanent classics, still beloved all over the world. Others come from weirdos experimenting for a tiny handful of fellow fanatics. But they all sound great today. So it’s time to celebrate the music of 1999. As a wise man once sang: Let’s don’t forget about it.

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Buckcherry, “Lit Up”

Ten years after the heyday of Sunset Strip glam metal, and eight years after the whole scene went up in flames like an Aqua Net bouffant, a band of dirty rocker boys calling themselves “Buckcherry” (a pun on “Chuck Berry”) revitalize every noble ideal the genre ever stood for. “Lit Up” revels in sleaze and spandex, right from the first line: “I’m on a plane with cocaine!” (Josh Todd keeps it so minimal lyrically, he’s the hair-metal Hemingway to Axl’s Faulkner.) Buckcherry had staying power — they didn’t reach their apex until the 2005 masterpiece “Crazy Bitch.” They got woke with the environmental plea “Our World” (sample lyric: “We keep on fighting for oil and killing in the Middle East”). Their 2014 EP Fuck consists of six songs with “fuck” in the title, including a metal cover of Icona Pop’s “I Love It” retitled “Say Fuck It.”

David Bowie during VH1 Storytellers - David Bowie, United States. (Photo by Ke.Mazur/WireImage)

Kevin Mazur/WireImage

48

David Bowie, “Thursday’s Child”

The Thin White Duke sings a modern-love space-soul ballad, as he turns 50 and meditates on his golden years with Iman. Bowie intended “Thursday’s Child” as a duet with TLC, but tragically, it never happened. Hours was an underrated gem that did for Nineties R&B what Young Americans did for Philly soul, and “Thursday’s Child” feels like a lost collabo between Babyface and Marc Bolan. Few appreciated at the time, but it was part of his creative rebirth after marrying Iman, in a run that included Earthling, Heathen and Reality. “Thursday’s Child” was also inspired by his teenage crush on Eartha Kitt, as he explains in his definitive VH1 Storytellers version, taking the title from her autobiography: “Some of my favorite bedtime reading. Not just my bedtime, truth be known.” No relation to Van Morrison’s “Friday’s Child,” except they’re both great. Somewhere up in the clouds, Bowie and Left Eye are lighting this one up.

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Hefner, “I Took Her Love for Granted”

True romance: “The taste of her tongue, it makes me wish I’d given up smoking.” Hefner were the very picture of a hyper-literate, hyper-neurotic, sex-obsessed English cardigan-core indie band, except twice as pretentious and ten times funnier. “I Took Her Love for Granted” is their valentine to a bookish dominatrix, a seven-inch single that prefaced a concept album about young lust, The Fidelity Wars. The girl in this song is infinitely cooler than any of the Hefner boys, but they’re sensible enough to realize it. Best line: “Can’t feel disappointed when her hips are that wide / But I still feel lonely and screwed-up inside.” It says something about the Nineties that a group as superb as Hefner could get lost in the shuffle, just because there was a worldwide glut of smart funny guitar bands.

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Handsome Boy Modeling School, “Metaphysical”

Underground rap pioneer Prince Paul had a hell of a year — a decade after he helped create the Daisy Age, he dropped two of 1999’s cult faves. A Prince Among Thieves was a hip-hopera about the life of a young MC. Handsome Boy Modeling School was his crazed sample-collage project with Dan “The Automator” Nakamura, to promote better grooming and fashion. As Prince Paul told Rolling Stone, it was an academy where “anyone with 60 bucks can have their handsomeness brought out.” On their album So…How’s Your Girl?, they teach their lessons with De La Soul, DJ Shadow, Del the Funky Homosapien, Kid Koala, Sean Lennon and Father Guido Sarducci. The highlight: “Metaphysical,” a style seminar from the Beasties’ Mike D and Cibo Matto’s Miho Hatori. It made the world a handsomer place, reminding everyone of the importance of manicures. As Dan the Automator explained, “It sucks to DJ a show and have your cuticles get caught on the turntables.”

THE BETA BANDTHE BETA BAND - 1998

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45

The Beta Band, “The Hard One”

The rustic Scottish beardos of the Beta Band sounded like they were fond of turntables, samplers, folkie guitars and maybe — just maybe — truckloads of drugs. “The Hard One” is the Betas’ 10-minute acid-bass dub drone, built on a slow-motion sample of Bonnie Tyler’s “Total Eclipse of the Heart,” looping those familiar piano notes into infinity while the singer drawls: “Once upon a time I was falling apart / Now I’m always falling in love.” Words to live by.

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Limp Bizkit, “Nookie”

The Durst-est of the Durst. The nu-metal clods in Limp Bizkit became the scourge of TRL Nation, breaking stuff and doing it all for the nookie. Their signature hit was the nu-metal “Thank U, Next,” a break-up song combining some of the decade’s most laughable rapping with a first-rate moron-rock chorus — “You can take that cookie and stick up your yeeeaaah!” Fred Durst chokes on his nookie issues until the guitars come along to kick him in the yeah. (It’s how PJ Harvey’s “Dry” might have sounded if she’d gotten produced by Dr. Dre instead of Steve Albini.) “Nookie” was so clever, people began to suspect Limp Bizkit were secretly smart. Then they called their next album Chocolate Starfish and the Hot Dog Flavored Water. Durst now hosts a jazz night at an L.A. lounge where Lady Gaga just showed up to do a surprise set of Frank Sinatra songs.

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Missy Elliott, “Hot Boyz (Remix)”

The third straight Summer of Missy — after “The Rain (Supa Dupa Fly)” in 1997 and Nicole’s “Make It Hot” in 1998, Missy and Timbaland had the whole world wired to their Virginia Beach hip-hop swamped-out trans-galactic funk. The “Hot Boyz” remix brought in a slew of all-stars: Nas, Q-Tip, Eve and Lil Mo, with cameos in the video from Mary J. Blige and Ginuwine. Missy gets her freak on with a proto-Meet Me in the Bathroom fetish — “You a hot boy, a rock boy.” She always pushes her collaborators, from Katy Perry at the Super Bowl to stealing the new Lizzo album. But in “Hot Boyz,” everyone is just trying to keep up with Missy. Nobody ever could.

Editorial use only. Consent for book publication must be agreed with Rex by Shutterstock before use.Mandatory Credit: Photo by Andre Csillag/REX/Shutterstock (452560bg)FLAMING LIPS ON 'LATER WITH Jools Holland ' TV SHOW, BRITAIN - NOV 1999VARIOUS

Andre Csillag/REX/Shutterstock

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The Flaming Lips, “Feeling Yourself Disintegrate”

Wayne Coyne and crew camped out in their own studio for two years making The Soft Bulletin. It capped an amazing decade for the Lips. Strange as it seems now, the Oklahoma dudes were still best known for their novelty hit “She Don’t Use Jelly,” which they lip-synched at the Peach Pit on Beverly Hills, 90210. “Momentarily it may have tricked us into thinking we could be the next, I don’t know, Stone Temple Pilots or something,” Coyne told me in 1999. “But a lot of bands have hits that size, and it derails their whole evolution. They start following something arbritrary, which they have no control over, as opposed to following their muse.”

The Lips followed their muse to “Feeling Yourself Disintegrate,” a gorgeously vulnerable stargazing ballad about mortality. (The kind of song Coyne later helped mentor Miley Cyrus to write for her concept album about her dead pets.) This year, the Flaming Lips will release their live performance of The Soft Bulletin with the Colorado Symphony, as well as their brand new King’s Mouth. “I never expect the audience to come along with us,” Coyne said then. “I’m always surprised.”

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Basement Jaxx, “Rendez-Vu”

The South London duo of Felix Buxton and Simon Ratcliffe blew minds with the sound they called “punk garage,” for a hugely innovative rampage through house music. “What we admire in deep house and American garage is the music’s untouchable sexiness, which U.K. house has always lacked,” Ratcliffe said. “At the same time, we like to rough up that polished sound with some English punk attitude.” They started making their own records in Ratcliffe’s basement studio, cooking up the world-beating debut Remedy. “Rendez-Vu” is a spine-rattling barrage of disco high-hat, vocoder pillow talk, flamenco guitar, the sound of feral cats mating on a turntable. Basement Jaxx have lived up to that punk garage spirit ever since. “Most dance music is very shiny and so robotic,” Ratcliffe told Rolling Stone. “There’s just not much feeling. If we made a record like that, we’d be just like everybody else.”

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Smash Mouth, “All Star”

Yep, what a concept. The San Jose golf bros in Smash Mouth might have looked like a one-shot fluke after their 1997 hit “Walkin’ on the Sun,” but “All Star” was a jock-rock pep talk cherished by anyone who’s ever felt like the dullest tool in the shed. It’s also a never-ending meme factory. (“SOOOOOMEbody once told me…”) Steve Harwell reminds us all that “glowing” takes epistemological precedence over “shining,” ergo “you’ll never shine if you don’t glow” — just stop throwing bread at the man, OK? “A lot of people said that we weren’t talented enough to do that type of shit,” Harwell told Rolling Stone at the time. “We did this record to let people know, ‘Hey, don’t fuck with us. We built this team and nobody’s going to take it away from us.’” Harwell’s “it’s a cool place” vs. Rob Thomas’ “man, it’s a hot one” added up to a trenchant radio dialogue on the climate crisis. Get your game on forever, Smash Mouth.

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Brian McKnight, “Back at One”

The Zen master of Nineties baby-making R&B slow jams. Brian McKnight has spent his noble career schooling less evolved males (i.e. all of us) in his esoteric wisdom of romance. In “Back at One” he counts all the steps to winning a woman’s heart. What happens when he gets to the end of the list? “If ever I believe my work is done, then I start back at one.” Not since the late great James Ingram in “One Hundred Ways” has a love man given such a sensual math lesson.

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μ-Ziq, “The Fear”

London electro composer Michael Paradinas was the brain behind μ-Ziq (pronounced “Mu-Ziq” and often styled that way). Like his mate the Aphex Twin — they used to listen to Philip Glass together — he hid in his home studio cooking up his abrasive ambient works, including cult classics like In Pine Effect. Paradinas explored jungle textures under names like Kid Spatula or Tusken Raiders, while running his own Planet Mu label. But “The Fear” shows the influence of touring with Bjork as her opening act. It’s a swirl of hypnotic disco strings and the coos of Japanese chanteuse Kazumi, over throbs of abstract drum-and-bass percussion. “The Fear” taps into a strange kind of alien melancholy that stays with you long after the music ends — a song that leaves you dizzy and disoriented and not sure why.

AIMEE MANNFLEADH FESTIVAL 2001, FINSBURY PARK, LONDON BRITAIN - 16 JUN 2001

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37

Aimee Mann, “Wise Up”

Mann had already built her hard-won following as a singer-songwriter, after her “Voices Carry” days with ‘Til Tuesday. But “Wise Up” became her most famous song with an unforgettable appearance in Paul Thomas Anderson’s L.A. ensemble Magnolia. Anderson used this ballad as the film’s emotional climax, as a cast full of lost souls all over the city— Julianne Moore, Jason Robards Jr, William H. Macy, Tom Cruise, Phillip Seymour Hoffman — sing it to themselves.

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Monica, “Angel of Mine”

The third (and best) Number One hit by the Atlanta girl who went to high school with 2Chainz but achieved mega-stardom before she got her diploma. As my fellow Nineties scholar Brittany Spanos has brilliantly theorized, “The Boy Is Mine” was the “Hunger Strike” of R&B, with Brandy as Eddie Vedder and Monica as Chris Cornell. But like the hair-twirling, bread-stealing dudes in Temple of the Dog, Monica and Brandy hit higher peaks on their own. “Angel of Mine” was Monica’s empathetic ballad; just to complete the grunge comparison, it was her equivalent to Soundgarden’s “My Wave.” She got “Angel of Mine” from the U.K. girl group Eternal, but she took the song to church, as well as to Number One for four weeks. Monica’s last album, Code Red, had her tough-talking Timbaland collabo “All Men Lie.” In totally unrelated news, she just filed for divorce from NBA star Shannon Brown. Stay strong, Monica.

MCGRATH SHEPPARD Singer Mark McGrath of the band Sugar Ray sticks out his tongue at guitarist Rodney Sheppard during the band's set at the annual KROQ Weenie Roast summer concert, at Irvine Meadows Amphitheater in Irvine, Calif. Sugar Ray performed with a variety of the most popular contemporary alternative rock acts including Limp Bizkit, Blink-182, Metallica and Red Hot Chili PeppersWEENIE ROAST CONCERT, IRVINE, USA

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35

Sugar Ray, “Every Morning”

The definitively crazed pop band, for this most crazed of pop years. Mark McGrath could fake it so real, he went beyond fake, right down to his frosted tips. “Even these fucking highlights in my hair are back in style again,” McGrath told me proudly last year. “Dude, if you stick with a bad hairstyle long enough, it’ll come back 20 years later.” When Mark showed up for his 1999 Rolling Stone cover shoot, he was so hungover and partied-out, his publicist begged him to keep his shirt on. Needless to say, it was on the floor in seconds. We airbrushed abs on him. Not only do I love “Every Morning,” I believe the great lost shoulda-been hit from their album 14:59 is “Ode to the Lonely Hearted,” yet I have never once convinced anyone to agree or even care, least of all the guys in Sugar Ray. I admit no hill is dumber to die on than Sugar Ray deep cuts, but I still think I’m right.

Black Star with a special guest Questlove performing for "Benefit for Nkiru Books" at the Knitting Factory on Saturday night, September 4, 1999.This image:Mos Def (Dante Terrell Smith).(Photo by Hiroyuki Ito/Getty Images)

Hiroyuki Ito/Getty Images

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Mos Def, “Brooklyn”

The conscious poet from the Rawkus scene was already revered for his Black Star collabo with Talib Kweli. But he got closer to home in Black on Both Sides, with an ode to his native Bucktown: “Brooklyn my habitat, the place where I happen at.” It’s a three-part suite, like the missing link between Paul’s Boutique and “Sicko Mode,” as Mos Def croons his own version of the Chili Peppers’ “Under The Bridge” (“the city I live in, this beautiful Brooklyn”) over producer Ge-ology’s jazzy vibraphone loop. By the end, he’s pouring one out for Biggie over the “Who Shot Ya?” beat, from Franklin Ave to Coney Isle, from Bushwick to Canarsie, from the Hook to the Stuy. Like Mos Def says, “I’m from the slums that created the bass that thump back.”

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Blur, “Coffee and TV”

Guitarist Graham Coxon was the prime mover in Blur’s late Nineties peak, taking their Pavement obsession to the bank in Blur and 13. (Blur are up there with Wilco in the annals of bands who got drastically better when they decided to turn into Pavement, right around the time Pavement were deciding to collapse.) On “Coffee and TV,” the bespectacled guitar nerd takes over from Damon Albarn to sing lead, over strum-along guitars echoing New Zealand bands like the Clean or the Verlaines, filtered through Brian Eno circa Taking Tiger Mountain. “Coffee and TV” is one of the most neurotic love songs ever, with Coxon yelping, “I’ve seen so much I’m going blind / And I’m brain-dead virtually.” It had a big moment in Cruel Intentions, as the song playing when Selma Blair and Sarah Michelle Gellar share their first kiss in Central Park.

Bill Callahan performing live at The Green Man Festival 2007 at the Glanusk Estate in the Brecon Beacons, Wales. 19th August 2007. Job: 31246 Ref: ZB2856_166550_0677EWT - Non-Exclusive  (Photo by Edd Westmacott/Photoshot/Getty Images)

Edd Westmacott/Photoshot/Getty Images

32

Smog, “Hit the Ground Running”

In one of the year’s least expected developments, indie wolfboy Bill Callahan, a.k.a Smog, became a halfway semi-quasi-functional human singer-songwriter on his masterful Knock Knock. It makes a perfect pair with Cat Power’s Moon Pix, in a classic he-said she-said tale of the same relationship. (Up there with Nick Cave’s The Boatman’s Call vs. PJ Harvey’s Is This Desire?) “Hit the Ground Running” begins with a very odd children’s choir (all those kids must be adults in therapy by now) and a ragged guitar, as Callahan sings about fleeing the country and heading back to the city after some kind of emotional apocalypse. But he vows to start over, stretching his Lou Reed guitar groove out to seven minutes: the overall effect is bizarrely uplifting. If it can happen to Smog, there’s hope for all of us.

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Cool Breeze, “Watch for the Hook”

The Dirty South rap blast of the year, from the man who originated the term “Dirty South” (on Goodie Mob’s Soul Food). Cool Breeze rounds up the Dungeon Family in “Watch for the Hook,” gathering friends like OutKast, Goodie Mob and Witchdoctor for an all-star anthem of Georgia pride, right at the moment when ATL took over. “Watch for the Hook” is one of Organized Noize’s most audacious productions, cutting up Neil Young’s “Southern Man.” But not Neil’s original — they go for the 1971 version by gospel singer Merry Clayton, famed for her vocals on the Stones’ “Gimme Shelter,” adding new levels of irony to the Ontario-via-New Orleans conga groove. (Especially since Clayton also sang on Lynyrd Skynyrd’s anti-Neil answer song, “Sweet Home Alabama.”) “Watch for the Hook” is a true Decatur psalm, with Cool Breeze coming in at the end to deliver the knockout punch: “My ones and my twos got your whole town shook / You better listen to your corner and watch for the hook.” No wonder T.I. has Cool Breeze’s album on display at his new Trap Music Museum in Atlanta.

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Lit, “My Own Worst Enemy”

These SoCal pop-punk dudes had quite the flair for wordplay: “You make me come / You make me complete / You make me completely miserable.” In “My Own Worst Enemy,” they came up with a timeless tale of bad decision-making, passing out drunk with their clothes on after saying the wrong thing. Lit are still in the pop-punk game — a few years ago they teamed up with Butch Walker to write a long-overdue “My Own Worst Enemy” sequel (“My car is in the front yard / I think I’ve been here before”) called “Same Shit, Different Drink.”

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The Roots, featuring Erykah Badu, “You Got Me”

The Roots had already built themselves a legend with their boho Soulquarian sound, but they scored their biggest hit in “You Got Me,” a mission statement for everything they’d accomplish over the next two decades. “You Got Me” was co-written with their Illadelph neighbor Jill Scott (still a year away from her own debut) and sung by Erykah Badu, with the not-yet-massive Eve rapping the second verse. It’s a melancholy romance that takes off at the end when Questlove rips into that drum solo — he seizes the sound of U.K. drum-and-bass digital snare rattles, but translates them into his own unmistakable language. Lost in music, lost in love.

Icelandic avant-rock band Sigur Ros, Reykjavik, Iceland, 1997. (Photo by Martyn Goodacre/Redferns)

Martyn Goodacre/Getty Images

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Sigur Ros, “Svefn-g-englar”

The Icelandic space-rockers in Sigur Ros arrived with an otherworldly sound: Jonsi Birgisson used a cello bow to draw spooky moans out of his guitar, while keening lyrics that veered from Icelandic to the band’s own made-up language. Sigur Ros were virtually unknown in the English-speaking hinterlands until Radiohead gave them a thumbs-up. Agaetic Byrjun (“A Fine Start”) begins with the ten-minute beauty “Svefn-g-englar,” which drones like “Cortez the Killer” as sung by a dying glacier. Even at its most opaque, the song has a very classic-rock sense of grandeur, like some kind of puffin prog. “We sometimes rock out,” bassist Georg Holm told Rolling Stone’s David Fricke. “But it takes a lot time to build up to it. Then suddenly we rock — and do that for a long time.”

madonna
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Madonna, “Beautiful Stranger”

“Beautiful Stranger,” from the soundtrack of Austin Powers: The Spy Who Shagged Me, was the second chapter of the trilogy Madonna began with Ray of Light and closed in Y2K with Music — the hottest musical run of her life. Just as Ray of Light remains the best pop album ever made by a 39-year-old, “Beautiful Stranger” is the most shagadelic disco hit by a megastar shimmying into the big 4-0. She really runs with the Sixties concept, tripping on Love’s flower-power classic “She Comes in Colors,” in a salute to then-incarcerated black hippie pioneer Arthur Lee. Madonna has never sounded so loose, so lithe, so funny. Best line: “If I’m smart then I’ll run away / But I’m not so I guess I’ll stay.”

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26

702, “Where My Girls At?”

The Missy Elliott jam of the year: the 702 girls call a meeting in the ladies’ room to issue a very Missy beatdown threat, explaining why they won’t hesitate to kick the ass of anyone who touches their guy. (“Trying to take my man? See, I don’t need that.” Got it, ladies.) 702 took their girl-group name from the area code of their native Las Vegas, where they got discovered by comedian Sinbad when he heard them harmonize in the lobby of Caesar’s Palace. Their Unsung episode is a must-see.

(MANDATORY CREDIT Ebet Roberts/Getty Images) UNITED STATES - JANUARY 01:  Photo of Randy NEWMAN  (Photo by Ebet Roberts/Redferns)

Ebet Roberts/Getty Images

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Randy Newman “Shame”

Randy claims his crown as the oldest, dirtiest bastard in rock & roll. At 55, the Hollywood piano man took a break from Disney movie soundtracks to make Bad Love, his nastiest and best album since the Nixon Administration. “Shame” is a New Orleans piano shuffle where he’s a sugar daddy wining and dining his fickle young thing, trying to woo her back to his mansion. “I’ve sunk pretty low this time,” he admits, though he’s got even lower to go. Newman sings “Shame” with a mean blues twitch — one of the great comic performances of his life. By the end, he mutters “You know, I have a Lexus now” in a haze of self-loathing lust. When I interviewed James Taylor for Rolling Stone that fall, this song was all he wanted to talk about. “Have you heard ‘Shame’? Can you fucking believe that thing? Holy shit! Unbelievable! I didn’t know if he could top the demo, but he stepped up to the fucking plate and knocked it out.” James Taylor is always right.

dixie chicks
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Dixie Chicks, “Goodbye Earl”

Murder songs are a country tradition that’s as old as the hills — but usually, the killers at least pretend to feel a tiny bit guilty about it. Not the Dixie Chicks’ style. The most shocking thing about “Goodbye Earl” is how fun it is, a rowdy hell-raising hoedown that just happens to be about putting an abusive husband six feet under. It’s hard to overstate what a bombshell “Goodbye Earl” was on country radio, even at a time when the format was driven entirely by female artists and female listeners. Then as now, the Chicks are way ahead of the pack.

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Santana featuring Rob Thomas, “Smooth”

Hey, maybe male rock stars would still be a thing if they studied “Smooth” for lessons in how to lavish praise on female smoothitude. Sixties guitar hero Carlos Santana meets the Matchbox 20 singer for an ode to a “Spanish Harlem Mona Lisa,” resulting in a Number One bubble-salsa smash that’s just like the ocean under the moon. Rob Thomas sounds confused, almost as if he just met a girl who gave him her heart but opted not to make it real. (Forget about it!) Yet his vocal is all tongue-tied boyish awe in the presence of womanly charisma, also captured in the way Santana bows down to the dancing muñequitas at the end of the video. Rob has a brand new album, Chip Tooth Smile. Even cooler: RT is still married to the woman he wrote this song about? An inspiration to us all. In this cold cruel world, “Smooth” remains the hottest of hot ones.

The Chemical Brothers at Glastonbury, UK, 2000'sSTOCK

Brian Sweeney/Pymca/REX/Shutterstock

22

The Chemical Brothers, “The Sunshine Underground”

The Chemical Brothers made one of the all-time great summer albums with Surrender, a flawless hour of techno headbang with a hippie-festival grin. Your superstar DJs: Ed Simons and Tom Rowland, a couple of lovably shaggy vinyl nerds from Manchester. They scored hits like “Setting Sun,” with Oasis’ Noel Gallagher. But “The Sunshine Underground” is their biggest bang, a nine-minute psychedelic explosion where vocoder angels harmonize with a sitar sample (from James Asher’s “Asian Workshop”), the synths cry out like Moroccan ghaitas and the breakbeats slam like Zeppelin in full-on levee-busting mode. The Chems were ahead of their time — a few years later, their sound was all the rage via NYC bands like LCD Soundsystem and the Rapture. Tom and Ed just dropped their excellent new album No Geography. But “The Sunshine Underground” is their utopian statement for the ages. This song was definitely my least traumatic moment of Woodstock ’99.

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Whitney Houston featuring Faith Evans and Kelly Price, “Heartbreak Hotel”

You can hear it in her voice: this woman has been through some shit. “Heartbreak Hotel” is Whitney at the peak of her late-game resurgence, in a divorce song that seethes with contempt — right down to the way she sneers the words “heart-break ho-tel.” It shows why Whitney just kept getting better in the Nineties — in a classic example of the Showgirls Principle, Whitney knew there were younger, hungrier divas coming down the stairs after her, so she knew it was time to sing for her life. (And she steals her hook from George Michael, which is just cold.) We all figured she’d go on making records this tough for years to come. But still only 35, she was coming to the end of her story.

rage against the machine
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Rage Against The Machine, “Sleep Now in the Fire”

Make America Rage Again. In “Sleep Now in the Fire,” RATM blast through the history of Western imperialism, from Columbus to the Zapatistas. Zach de la Rocha fights the power — “I am the Niña! The Pinta! The Santa Maria!” — while Tom Morello makes his guitar screech like crosstown turntable traffic. When Seattle exploded in November 1999 with the World Trade Organization protests — “The Battle of Seattle” — Rage seemed prophetic. But their music sounds timelier than ever now. At the MTV Video Music Awards in 2000, when Rage lost to Limp Bizkit, bassist Tim Commerford protested by climbing the 20-foot fake palm tree onstage during Fred Durst’s speech and refusing to come down. He spent the night in jail. Rage broke up a month later. Commerford didn’t apologize to Limp Bizkit, but he recently told Rolling Stone, “I do apologize for Limp Bizkit. I really do. I feel really bad that we inspired such bullshit.”

juvenile
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Juvenile, “Back That Azz Up”

Juvenile rises out of the Magnolia to announce, “Cash Money taking over for the Nine-Nine and the 2000!” A pioneering Southern bounce anthem that sold the rest of the country on the New Orleans sound — his street flow was as raw as in his previous “Ha,” but this time Juvenile focused on the dancing girls, especially the lower half: “You a fine motherfucker, won’t you back that azz up?” (The radio version nervously changed it to “Back That Thang Up.”) Lil Wayne steals the show. In his classic outro, quoted by everyone from Nicki to Snoop, he drops it like it’s hot.

red hot chili peppers californication
17

Red Hot Chili Peppers, “Californication”

The Chili Peppers surprised everyone by coming back with their best song ever, finishing the L.A. soft-rock trilogy they began with “Under the Bridge” and “Soul to Squeeze.” (You remember, from the Coneheads soundtrack.) After a few lost years, they reunited with long-lost axeman John Frusciante, playing a 1955 Gretsch White Falcon he got from filmmaker Vincent Gallo. In “Californication,” Anthony Kiedis sings about decadence and despair under the palm trees: “Space may be the final frontier but it’s made in a Hollywood basement/Cobain, can you hear the spheres singing songs off Station to Station?” Frusciante plays his gorgeously elegiac guitar as bold as love.

Destiny's Child Performing Live On Stage at Pnc Arts Center in Holmdel New Jersey September 6 2000VARIOUS

Rtcanova/Mediapunch/REX/Shutterstock

16

Destiny’s Child, “Hey Ladies”

Beyoncé begins “Hey Ladies” with the commandment: “Thou Shalt Know When They Have to Go.” Her 1999 prequel to “ashes to ashes, dust to sidechicks”? Destiny’s Child changed the game with their futuristic R&B, all hyper-staccato sci-fi electro-beats and vocal hiccups. It was a world away from singer-centric Nineties radio — not far from the robot sound Max Martin was simultaneously trying out with Britney. The initial hits from The Writing’s on the Wall were underwhelming, but fiends flipped for twist-baby-twist deep cuts like “Hey Ladies.” Bey catches her man sneaking around with some tenderoni, raging over Kevin “She’kspere” Briggs’ jealous-again synth-spurts. LeToya and LaTavia chant “He’s got to go, he’s got to go,” even though they were the ones on the way out. Way to hang in there, Michelle. Welcome, Kelly. And don’t get too comfortable, Farrah.

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15

Kid Rock, “Cowboy”

Kid Rock introduced himself with everybody’s favorite radio-rock record of the year, Devil Without a Cause, a glorious one-shot blast of Motor City madness. In “Cowboy” he trucks out west to start an escort service for all the right reasons, mixing up butthead metal, Sugarhill rap, midnight-rider blues twang and the piano solo from the Doors’ “L.A. Woman.” It was like the second coming of Diamond Dave. After Devil made him a star, the Kid went in the opposite direction: He purged the hip-hop and metal, became a soft-rock crooner, sucked up to right-wing politicians, made a sex tape with the singer from Creed. But for a brief and shining moment there in “Cowboy,” he just wanted to cause chaos and rock like Amadeus for his Detroit playas. R.I.P., Joe C.

NEW YORK - FEBRUARY 1997: American rap artist ODB (Ol' Dirty Bastard) of the rap group Wu-Tang Clan poses for a February 1997 portrait in New York City, New York. (Photo by Bob Berg/Getty Images)

Bob Berg/Getty Images

14

Ol’ Dirty Bastard featuring Kelis, “Got Your Money”

Preach, Big Baby Jesus: “I don’t have no trouble with you fuckin’ me, but I have a little problem with you NOT fuckin’ me.” The Wu-Tang Clan’s loosest cannon brings all his pimp slobber, in a hit dedicated “to all the pretty girls of the world, and all the ugly girls, too.” ODB sounds extra deranged over the Neptunes’ high-gloss funk, plus a hook from one of the year’s brightest newcomers, Kelis. The Neptunes and Kelis were on the come-up; sadly, Dirty was on the way out. Wu-Tang might be for the children, but this song definitely isn’t. As RZA told Rolling Stone, “When it came time to assemble the album, we listened to a lot of old Blowfly and Richard Pryor tapes, just buggin’ out. I told Elektra that ODB wants a Grammy, but fuck going for the hip-hop Grammy; this shit is funny — let’s go for the comedy Grammy!”

Editorial use only. Consent for book publication must be agreed with Rex by Shutterstock before use.Mandatory Credit: Photo by Andre Csillag/REX/Shutterstock (481524iw)PAVEMENT PERFORMING ON 'LATER WITH JOOLS' ON BBC TV - OCT 1999VARIOUS

Andre Csillag/REX/Shutterstock

13

Pavement, “Harness Your Hopes”

The Nineties’ greatest guitar tricksters had one last album in them before falling apart, Terror Twilight, with Radiohead producer Nigel Godrich—full of hippie jams and doofy harmonica solos. Nobody realized the harmonica man was Jonny Greenwood. “I didn’t know that Nigel album was gonna be so Nigel-ed out before I did it,” Stephen Malkmus told me in 2001. “I like it, but I didn’t want to do that again.” It had ballads like “Major Leagues,” about facing up to your thirties and leaving youth behind—as he sang, “Cater to my walls and see how they fall.” But the best thing Pavement released all year was the B-side “Harness Your Hopes,” a wild guitar romp with no maturity, no introspection, no sincerity at all. Just Malkmus back on his slack bullshit, with sighs and cackles and rapid-fire word slop (“don’t telegraph your passes, you’ll end up with molasses” etc.) over that Creedence-via-Velvets choogle. Most beautiful moment: when he squawks “the shroud is made of linen!” for no reason at all. And they left this masterpiece off the album—a perfect self-sabotage for this band.

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12

Le Tigre, “Hot Topic”

Bikini Kill warrior Kathleen Hanna formed this punk supergroup with zine writer Johanna Fateman and indie filmmaker Sadie Benning, just a few years after Bikini Kill signed off with Reject All American. Le Tigre came out of left field to knock everyone sideways with their November 1999 debut album — like Fugazi 10 years earlier, they rode in at the end of the decade, revitalizing the best elements of their past projects for a tough march into the future. And like Fugazi, they gave a new hope to kindred spirits. “Hot Topic” is a riot grrrl slumber party of new wave beats and playground chants, shouting out a roll call of their feminist heroes, both famous and un: “Gertrude Stein!” “Yoko Ono!” “Billie Jean King!” “Ann Peebles!” “Ut!” “Carolee Schneeman!” “The Slits!” “James Baldwin!” “Ariel Schrag!” “Angela Davis!” And most importantly, over and over: “We won’t stop!”

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11

Eve, “Gotta Man”

“Gotta Man” showcased the Ruff Ryders’ First Lady, the “pit bull in a skirt,” with the most iconic tattoo in Nineties hip-hop. (Paw-prints!) The blonde Philly rapper got her start dancing in a Bronx strip club; Mase, of all people, was the customer who advised her to get out of there and rap. “Gotta Man” was her maddeningly catchy jump-rope rhythme, over a Swizz Beatz loop of acoustic guitar and rat-tat-tat snares. He originally planned “Gotta Man” for Aaliyah, but Eve takes over with life-hack tips on how she keeps her dogs on a short leash. (“Curse him out on the regular, just to make him sick”—Eve probably knows what she’s talking about here.) Let There Be Eve made her the third female rapper to score a Number One album, right after Lauryn Hill and Foxy Brown; her underrated UPN sitcom was definitely better than the one where LL Cool J played a nanny. Eve currently makes chitchat every morning with Sharon Osborne on The Talk. But with “Gotta Man,” she left her paw-prints on history.

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10

Backstreet Boys, “I Want It That Way”

Who holds the record for the longest gap between Number One albums? A gent by the name of Paul McCartney, who topped the charts with Tug of War in 1982 and Egypt Station in 2018. But second place now belongs to the Backstreet Boys, who just debuted at Number One with DNA 18 years after Black and Blue. “I Want It That Way” will always be their most famous song, as it deserves to be. This song will outlive us all, despite oblique lyrics that could have been written by Gertrude Stein. The video’s mise en scene raises the semiotic question of why Kevin keeps turning his back on the poor girl holding the “Kisses for Kevin” sign. (He greets literally every other girl in the video!) As for what “that way” means, leave it to your filthy imagination.

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Kelis, “Caught Out There”

One of the most shocking sounds to ambush the radio in 1999: Kelis vamps an R&B break-up jam that builds to the chorus where she flips out and yells, “I hate you so much right now!” She spits each syllable individually, in case you missed it. As she told Rolling Stone, “Cheating was a concept that everyone could relate to.” Kelis was a 20-year-old newcomer, so her debut single had the element of surprise—her voice is a ticking time bomb. The Neptunes’ production is a luxuriant caress of sex and bass and sweat, until Kelis turns into a one-woman Hate Unlimited Orchestra, screaming with fury that would have been unthinkable for radio airplay just a couple years later. In the video, she leads a women’s march in the streets. “Caught Out There” was years ahead of its time, to say the least. It sounded like nothing else then—and it remains a song that refuses to fade into the background.

blink 182
8

Blink-182, “All the Small Things”

Fact: Tom DeLonge is STILL MARRIED to the punk rock girl who left him roses by the stairs. Keep it crunk, you crazy kids. Tom is NOT still commiserating with the other two guys in Blink-182, but you can’t have everything. With “All the Small Things,” these SoCal jokers became the pop-punk heart-throbs they were always meant to be. As Mark Hoppus told Rolling Stone’s Gavin Edwards, “We’re kind of like Fisher-Price: My First Punk Band.”. They streaked into MTV with a TRL-ready video mooning NSync, the Backstreet Boys and Britney. But this song was explicitly pro-girl in ways that really resonated at the time, as Tom bonds Joey Ramone-style with his overworked, underpaid, florally sensitive, feminist punk muse. “He’s really straightforward,” Hoppus said. “He hangs out with his girlfriend and he believes in aliens.” Twenty years later, Tom’s chasing aliens on TV while the rest of Blink-182 plays Vegas. Turn the lights off, carry me home.

lfo
7

LFO, “Summer Girls”

In a summer when ridiculousness was the ultimate pop virtue, LFO managed to out-ridiculous everyone else with “Summer Girls.” LFO were three Boston dudes (it stood for “Lyte Funkie Ones”), with Rich Cronin rapping over an acoustic guitar lick that got sicker than Chinese food. LFO came on like a teen-pop Spinal Tap, dropping science like “Fell deep in love but now we ain’t speakin’ / Michael J. Fox was Alex P. Keaton” or “I like Kevin Bacon but I hate Footloose.” (How is that take even possible?) “Summer Girls” became a Number Three smash, even though MTV wouldn’t touch it with a ten-foot pole. (Maybe not a huge surprise, given how LFO sang about Carson Daly’s ex Jennifer Love Hewitt in their sequel “Girl on TV.”) Sadly, Rich Cronin died of leukemia in 2010; bandmate Devin Lima died in 2018. Rest in peace: we know they’re in a better place, surrounded by the color purple, macaroni and cheese, ruby red slippers and a bunch of trees. But LFO will live on forever in “Summer Girls,” a song that never fails to steal your heart and your bike.

fiona apple
6

Fiona Apple, “Paper Bag”

The centerpiece of her masterful second album When the Pawn, and still the most extraordinary machine she’s ever built. Fiona’s got every tiny whisper and sigh of “Paper Bag” timed so precisely, so unnervingly funny, so deeply sad, with piano chords from the Beatles’ White Album. It’s hard to overstate how much everybody planned on laughing at this album — with that 90-word title, people expected a hilarious flop. Then we heard the music and shut up. No matter how many times you’ve heard “Paper Bag,” it can still stop you cold in your tracks. Fiona dissects a trifling lover — “I thought he was a man, but he was just a little boy” — yet she’s glad to be herself instead of him, even if she’s still a mess nobody wants to clean up. “Paper Bag” is the sound of the pawn turning into the queen.

jay big pimpin
5

Jay Z, featuring UGK, “Big Pimpin’”

Jay-Z makes “Big Pimpin’” a utopian statement of hip-hop unity around the globe—Brooklyn’s finest goes South to team up with the Texas duo UGK and the man from the big V-A, Timbaland. For the video, they take a love boat to Trinidad for Carnival. Underground kings Bun B and Pimp C shine in their bars—though Pimp C hated the beat, so he refused to show up for the video. Timbaland makes it ring with that Egyptian orchestral flute loop—sampled from “Khosara Khosara,” which he found on a compilation of belly-dancer soundtracks. (It’s kept “Big Pimpin’” in court ever since, in one of hip-hop’s longest-running legal battles.) “Some [lyrics] become really profound when you see them in writing. Not ‘Big Pimpin’.’ That’s the exception,” Hov said in 2010. “What kind of animal would say this thing? Reading it is really harsh.” Ms. Knowles had no comment.

sleater-kinney
4

Sleater-Kinney, “Get Up”

The greatest American punk band ever, in their most giant-hearted song. Sleater-Kinney staked out their turf with the rebel-girl bombshells Call the Doctor and Dig Me Out. But in “Get Up,” the Portland trio rushed into new territory, with Carrie Brownstein and Corin Tucker trading off vocals while stretching out for an urgent twin-guitar groove. “Get Up” is a song about mourning the broken pieces of your soul that you’ve scattered behind you, wishing you had some of them back, wondering if you might have one more hour to run back and search for them. Janet Weiss’ drums are the heartbeat that keeps reminding you to move forward, while you still can. It’s a noise only these three women could make.

britney spears
3

Britney Spears, “Baby One More Time”

An ordinary small-town American girl leads a secret life as an avenging angel of lust and dread: Welcome to Planet Britney. “Baby One More Time” was a song that changed the world, kicking off the teen-pop revolution. Britney, a 17-year-old ingenue from Kentwood, Louisiana, snarled her “oooh baby, baby” in a brat-dragon voice full of demands. Max Martin brought the disco thunder. The idea might have been pop, but the sonic philosophy came straight from Motorhead: as Lemmy would say, Everything Louder Than Everything Else. This song shut down the Nineties the way Led Zeppelin’s debut shut down the Sixties in January 1969—the blare and bombast so overwhelming, it was easy to miss the finely tuned details that made it go. But “Baby One More Time” remains a scary sound—the power is all in Brit’s demon growl. This song is where 21st century pop begins.

len steal my sunshine
2

Len, “Steal My Sunshine”

The most perfect of all summer hits, from the hottest summer ever for Top 40 radio. Len were a couple of Toronto punk kids, Marc “The Burger Pimp” Costanzo and his little sister Sharon. She explained their division of labor in Details: “Marc is Mr. Music Man — I just shake my rack.”

“Steal My Sunshine” was their ode to butter tarts and slurpy treats, skating on a disco piano loop. Marc, a guitarist who played in Sum 41, wrote “Steal My Sunshine” after a druggy three-day rave where Broken Social Scene’s Brendan Canning was DJing and put on a Seventies porn-disco classic, “More, More, More” by the Andrea True Connection. He loved the piano break, sampled it, woke up his kid sis and made her sing to give it that Human League “Don’t You Want Me” vibe. They figured nobody would ever hear it. “Steal My Sunshine” got barely noticed when it first came out, but it blew up L-A-T-E-R that summer on MTV. This song has it all: amateur rapping, tone-deaf singing, boy/girl solidarity, sibling bonding. (It was so startling to see a brother and sister hug on MTV in those days of Family Values Tour angst.) Len never had a second hit and nobody cared, not even them, because there’s no way to improve on this one. “Steal My Sunshine” still sounds like a million miles of fun.

tlc no scrubs
1

TLC, “No Scrubs”

Oh yes, son — they’re talking to you. T-Boz, Chilli and Left Eye — the Nineties’ premier pop group — strut into the future with their heads held high in “No Scrubs,” talking shit about any guy dumb enough to get in their way. The crazy-sexy-cool Atlanta girls hit Number One with a feminist hip-hop anthem about street harassment, an instant classic that has never left the radio. After all TLC’s ups and downs, from stardom to bankruptcy to Left Eye burning down her boyfriend’s mansion, “No Scrubs” had the right defiant tone. But today it sounds downright prophetic.

Everybody aspires to sing “No Scrubs,” from Kacey Musgraves to Rivers Cuomo. Chilli just appeared at Coachella to do it with Weezer. “Clearly, they’re not scrubs,” she told Rolling Stone’s Brittany Spanos. Producer Kevin “Shek’pere” Briggs co-wrote it with two members of Xscape, Tameka “Tiny” Cottle (now married to T.I.) and Kandi Burruss. (She also wrote NSync’s “It Makes Me Ill,” which means she got a writing credit when Ariana Grande sampled it for “Break Up With Your Boyfriend, I’m Bored.”) It’s steeped in hip-hop history, with nods to Kool Moe Dee (“They Want Money”) and Roxanne Shante (“Brothers Ain’t Shit”). The album version had Left Eye’s scrubphobic rap; the radio usually left it out. But “No Scrubs” talks tough either way: a group of very different women banding together against a hostile world, three señoritas stepping on your Filas.

“As women, we go through things every day, all day,” Kandi Burruss recently told NPR. “No matter where we go, somebody is gonna try to push up or try to holler at you, and they’re not always a gentleman about it. So I feel like this song put it out there…and it just made women be a little bit more outspoken.” “No Scrubs” still gets that job done. Crazy. Sexy. Most of all, cool. TLC, meant to be, forever.

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