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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

Ron Davis/Getty Images, Larry Busacca/WireImage, Andy Willsher/Redferns/Getty Images

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.

UNITED KINGDOM - JANUARY 01:  BRIXTON ACADEMY  Photo of FATBOY SLIM  (Photo by Nicky J. Sims/Redferns)

Nicky J. Sims/Redferns/Getty Images


Fatboy Slim, “Praise You”

What could sum up 1999 better than “Praise You”? An English techno DJ digs up an obscure Seventies hippie-gospel hook, bombards it with go-go breakbeats and computer blurps and Nashville honky-tonk piano. Result? A pop smash everybody and their mother loves. Norman Cook, a.k.a Fatboy Slim mixed a whole armful of rare wax — most prominently, Camille Yarborough’s voice — into a song that sounded at home in a club, a minivan, a day-care center, a druggy after-hours bar or a dollar-an-hour Internet café.

The video from Spike Jonze and Roman Coppolla captured the vibe, as the Torrance Community Dance Group interpreted it with a boombox outside a Southern California multiplex. At other points in history, “Praise You” would have been considered a weird little art project. But in 1999, it was the mainest of the mainstream, loaded with populist positivity and just a hint of pre-millennial tension. The perfect song to start the ride through this beautifully bizarro year.

q tip

Q-Tip, “Vivrant Thing”

When A Tribe Called Quest called it quits, it marked the end of an era. Q-Tip’s first solo hit took fans by surprise, as the Abstract swerved into a flashier, blingier lane. Many believers felt scandalized — see Hanif Aburraqib’s Go Ahead in the Rain for the full story. But as Tip said, “Progressing is if you move yourself into a different place and you’re on a search or a quest — pardon the pun.” “Vivrant Thing” takes the Native Tongues spirit to the club, with J Dilla flexing a Barry White groove.

X 134849-02  Jack White and Meg White.  Obligatory Credit - CAMERA PRESS/Mark Shenley.  The guitarist,  Jack White and drummer, Meg White are the minimalist rock duo from Detroit, 'White Stripes';  seen here during a concert at the London Astoria on 21/11/2001. The band was formed in 1997, with the aim to make simple rock and roll music. Although grounded in punk and blues, they strive for simplicity and American folk music; and evocative lyrics not present elsewhere in modern punk. Their self-titled debut album came out in 1997, followed by 'De Stijl' in 2000 and 'White Blood Cells' in 2001. The nature of the relationship, if any, between Jack White and Meg White remains a mystery.

Mark Shenley/Camera Press/Redux


The White Stripes, “Astro”

Meet Jack and Meg White: just a couple of fresh-faced Catholic kids from Detroit in matching red/white outfits, playing the blues. Such sweet moppets — they even dedicated their zero-budget indie debut album to the memory of the late bluesman Son House. Nobody guessed the White Stripes would blow up into the next decade’s biggest band. Or that the brother/sister act was secretly a divorced couple. “Astro” is raw and violent — Meg manhandles her drums while Jack dives deep into his guitar fetish, squealing in a voice full of Dolly Parton and Marlene Dietrich. Their rock & roll adventure was just beginning.

macy gray

Macy Gray, “I Try”

Sorry, Marilyn Manson: As soon as Macy Gray hit the airwaves with “I Try,” America had a new favorite freak-show scream queen from Canton, Ohio. And like Manson — her former high-school classmate! — Macy knew how to grab attention. “I Try” is her big prisoner-of-love ballad, as she sings in a rasp that mixes Billie Holiday, Erykah Badu and Klondike Kat. Macy’s 2012 album Covered has her jazzy versions of My Chemical Romance’s “Teenagers,” the Yeah Yeah Yeahs’ “Maps,” and Radiohead’s “Creep.” A damn fine Texas Hold ‘Em player, Macy competed on Bravo’s Celebrity Poker Showdown, going up against Joy Behar and Christopher Meloni.

south park

South Park, “It’s Easy, M’Kay”

South Park Elementary School’s guidance counselor Mr. Mackey teaches the kids a valuable lesson, mmm’kay? He has a song to reach their fragile little minds: “You don’t have to spend your life addicted to smack! Homeless on the streets, giving handjobs for crack!” Everybody in 1999 went to see South Park: Bigger, Longer & Uncut, the summer’s funniest movie, though it had stiff competition: American Pie, Austin Powers: The Spy Who Shagged Me, Cruel Intentions, Go, Dick, Ten Things I Hate About You. Quite a summer for cinema. But did any of those flicks have sheer poetry like “Eat penguin shit, you ass-spelunker”?


The Offspring, “Why Don’t You Get a Job?”

Oh, the zany days of the Nineties full-employment economy — in the Clinton-era boom, as the jobless rate reached historic lows, a rock band could turn a sentiment like this into a jolly sing-along TRL hit. The Offspring had quite a run of grunge bangers after emerging from the SoCal hardcore scene with “Self Esteem” and “Come Out and Play (Keep ‘Em Separated),” giving us proverbs like “I might be dumb, but I’m not a dweeb.” “Why Don’t You Get a Job?” is their hard-ass discourse on how to tell scrubs to get off the couch and chip in for the bills, bills, bills. Yet it bounces like a tribute to Swedish-produced teen-pop — possibly the first rock hit to rip Max Martin.

mo thugs

Mo Thugs Family, “Ghetto Cowboy”

Peak Yeehaw. The Bone Thugs & Harmony crew got their horses in the back and slapped on their cowboy hats for this proto-“Old Town Road” hip-hop smash. Krayzie Bone and Layzie Bone ride out west to a harmonica groove, singing a country hook from Kenny Rogers (the Original Gambla), boasting, “I be a rootin’ tootin’ shootin’ damn fool.” On the trail, they meet a cowgirl named Thug Queen, the best horse thief in these parts, so she joins the posse, they rob a bank with Powder P and Black Jack, then ride off to the saloon for some moonshine. Sing it, party people: “Giddy up, giddy up!” Note: “Ghetto Cowboy” topped the rap singles chart for eight weeks, just a couple of months before Lil Nas X was born.

brad paisley

Brad Paisley, “He Didn’t Have to Be”

Brad Paisley wrote his first hit after listening to a buddy talk about his stepson. Brad told him, “Let’s make a song about you two that will make your wife cry.” Fact: This is always the right way to write a country song. That’s why this West Virginia boy zoomed straight to Number One and has basically parked there ever since. Paisley gets it, and he’s been making wives cry for the past thousand American Saturday nights. (He made the rest of us cry with “Accidental Racist.”)

Counting Crows - Adam DuritzThe Werchter Festival Rock

Counting Crows - Adam Duritz The Werchter Festival Rock



Counting Crows, “Colorblind”

It’s a simple formula: First you blow your nose, and then you start singing about how if you were Picasso you’d buy yourself a gray guitar and play. But Adam Duritz had the bold idea to reverse the formula, and it made him a legend. We don’t talk enough about how This Desert Life is the Crows’ best album. Actually, we probably talk about it the exact right amount, which is every dozen long Decembers or so, but it’s true. “Colorblind” is the poignant piano ballad where Duritz muses, “I am covered in skin/No one gets to come in.” It made a big appearance in Cruel Intentions, when Reese Witherspoon spots Ryan Philippe waiting at the top of the escalator. (“I’m impressed.” “Well, I’m in love.”)  I forgot how great “Colorblind” is until I saw a friend lip-synch it at a drag show this winter — more proof that Adam Duritz will always be someone just a little more funky.

The Beastie Boys - Mike D, Ad Rock and MCA in PortugalVARIOUS - 1998

Andrew Testa/REX/Shutterstock


The Beastie Boys, featuring Miho Hatori, “Start!”

The Beasties were on such a roll, they could bang out brilliance like this as a bong-break throwaway. Nothing too complex going on here — just Mike D, Ad-Rock and MCA mucking around in the studio, doing a spliffed-out lounge-funk instrumental of the Jam’s 1980 mod-punk classic “Start!” They goose it with Hammond B-3 organ worthy of Jimmy Smith or Groove Holmes and some touchingly melancholy reggae melodica. Cibo Matto’s Miho Hatori coos the hook: “If I never ever see you agaaaiiin.” They probably spent twenty minutes total on this track and forgot it the next day, but it speaks volumes about what the Beasties and their music were all about.

beth orton

Beth Orton, “Stolen Car”

Beth Orton got her start as the voice of “folktronica” — with her acoustic guitar and her sullen English delivery, she got discovered by techno producer William Orbit, singing a Françoise Hardy ballad over drum loops. She won the hearts of club kids with her dazed vocals on the Chemical Brothers’ early records — she was the ideal comedown poet for a hangover lullaby like “Where Do I Begin?” For “Stolen Car,” Orton goes in a rootsier direction, stripping it down to a bongo beat and scratchy electric guitar from Ben Harper. She pines for a lover with cinnamon eyes and a face like a stolen car, going for the vibe of Court and Spark for a post-rave world. Good question, Beth: “Why should I know better by now/When I’m old enough not to?”

joey mcyntire

Joey McIntyre, “I Love You Came Too Late”

One of 1999’s coolest trends: The New Kids on the Block started scoring solo hits. About damn time, since ‘NSync and the Backstreet Boys were updating the boy-band template, while LFO were on the radio chanting “New Kids on the Block had a buncha hits/Chinese food makes me sick.” Jordan Knight brought the right stuff to “Give It to You” and a slow-jam cover of Prince’s “I Could Never Take the Place of Your Man,” while Joey Mac put you in a trance with a funky song called “I Love You Came Too Late.” The New Kids practically invented the fan cruise; they also invented the fan-cruise reality show, with Rock This Boat. This summer, they will hit the road for the Mixtape Tour with Tiffany, Debbie Gibson, Naughty By Nature and Salt-N-Pepa. Joey Mac has also been hanging tough on Broadway, starring in the musical Waitress.


Ginuwine, “So Anxious”

For a beautiful moment in R&B history, all the best slow jams were about two-way pagers, and Ginuwine’s “So Anxious” is one of them. It’s his second-most famous hit, which is no disgrace when the top spot belongs to “Pony.” The Virginia bachelor sits alone in his mansion, waiting in the bubble bath, feeling “So Anxious” because his girl isn’t paging him back even though his saddle is waiting for a pony ride. (No wonder Drake sampled this.) Timbaland makes a rare move into full-on Quiet Storm mode, with a bluesy guitar over his miles-deep reverb. The song ends with a sadder but wiser Ginuwine, still alone, still yearning for some equine action. What a chorus: “Girl, could you quit this stallin’?/You know I’m a sexaholic.”

UNSPECIFIED - CIRCA 2000:  Photo of Conor OBERST; performing at the "Bring 'Em Home Now! Concert"  (Photo by GNA/Redferns)

GNA/Redferns/Getty Images


Bright Eyes, “A Perfect Sonnet”

Conor Oberst was still in his teens, strumming his acoustic guitar in his parents’ basement out in Omaha. But even at this tender age, he’s a master of the choked sob — he barely gets through a syllable of “A Perfect Sonnet” without a sniffle or two. It’s his first great song, from the Every Day, Every Night EP, emoting in the fab voice of a heartland Robert Smith. Hyperbolic, hyper-dramatic, hyper in pretty much every way: The Bright Eyes lifestyle might not be something Conor would recommend, but it is one way to live. “A Perfect Sonnet” has one of his most perfect lines: “You know that she’s gone, because she left you a song.”

pet shop boys

Pet Shop Boys, “You Only Tell Me You Love Me When You’re Drunk”

The Pet Shop Boys try their hand at a country ballad — maybe someday Willie Nelson will cover it, the way they covered his “Always on My Mind.” Neil Tennant and Chris Lowe were already the grand old fops of U.K. New Wave synth-pop, prepping their musical Closer to Heaven. (Cardi B is a ride-or-die Pet Shop Boys fan — her fave is “Rent,” which makes all the sense in the world.) “You Only Tell Me You Love Me When You’re Drunk” has the droll wit of their 1993 masterpiece Very, the finest “wait, I’m turning 40 and I forgot to come out” album of all time. What have we done to deserve this?


Casiotone for the Painfully Alone, “Rice Dream Girl”

The essence of indie romance, circa 1999: A sad boy mumbles his diary into his bedroom four-track, along with a cheap toy synth. Owen Ashworth, under the excellent name Casiotone for the Painfully Alone, released Answering Machine Music on his label Cassingle USA, with titles like “Secretest Crush” and “Casiotone for the Painfully Alone Joins the French Foreign Legion.” “Rice Dream Girl” is his tragic ballad of love at the supermarket, when he meets that special someone while she’s buying rice milk in Aisle Four: “In an attempt to get my groove on/I offered you my White Castle coupon.” Sadly, it all goes wrong (“The radio was playing Seal/I tried to tell you how I feel”), but at least they share a moment when their shopping carts lock wheels. It’s probably no coincidence this song dropped the year LiveJournal was invented.

The DonnasThe Donnas - 01 Jan 1999

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The Donnas, “You Don’t Wanna Call”

Four born-innocent California girls, bashing out mall-rat punk with a zero-tolerance policy for scrubs. Donna A., Donna R., Donna F. and Donna C. became a staple of Hollywood teen movies, playing the prom in Jawbreaker and doing the REO Speedwagon love theme to Drive Me Crazy. But they sounded like fans who thought the Ramones and Motley Crue were essentially the same band. (On Get Skintight, they even covered “Too Fast For Love.”) “You Don’t Wanna Call” is their poignant break-up song: “Am I not old enough, am I too young/You think I don’t know how to eat dim sum.” Their next album was called The Donnas Turn 21.

Eddie Vedder of Pearl Jam at Neil Young's Bridge Benefit 1999 Finale at Shoreline Amphitheater in Mountain View Calif. on October 31st, 1999.  Image By: Tim Mosenfelder/ImageDirect

Tim Mosenfelder/ImageDirect/Getty Images


Pearl Jam, “Last Kiss”

Like Keanu Reeves in The Matrix or Bruce Willis in The Sixth Sense, Pearl Jam came back strong in 1999 with “Last Kiss.” The original “Last Kiss” was a cheesy 1964 teen-death oldie. (“Where oh where can my baby beeee? The Lord took her away from meeee!”) But Pearl Jam covered it affectionately on No Boundaries, a charity album to benefit Kosovo war refugees. To the shock of the band and pretty much everyone else, “Last Kiss” became their highest-charting hit ever. Eddie Vedder turns it into a Sixth Sense-style ballad about talking to dead people — he could be singing to Kurt, to Seattle, to some other part of his youth he’ll never get back. But when he sings, “Hold me, darling, just a little while,” he means exactly what he says.