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.

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

Pat Johnson/REX/Shutterstock


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.


Manishevitz, “Lonesome Cowboy Dave Thomas”

A lost classic from art-punk guitarist Adam Ostrar (then going by Adam Busch) with his Virginia band, on the then-fledgling Jagjaguwar label. “Lonesome Cowboy Dave Thomas” rides a primal Can-style Krautrock groove, yet it stretches out for eerie prog-folk in the mode of Robert Wyatt or Kevin Ayers. (The title is a tip of the cap to Pere Ubu and the Velvets.) Ostrar really puts on the chill when he moves to the chorus: “I am the walrus after work/And I am in the middle of a terrible divorce.” Now based in Austin, Ostrar has kept making his own unique music, including this year’s excellent The Worried Coat. “Lonesome Cowboy Dave Thomas” might be the most obscure song on this whole list — but once you hear it, it’s never forgotten.

BeckBWR's 1999 Oscar Awards PartyMarch 21, 1999 : Los Angeles, CA.Beck BWR's 1999 Oscar Awards Party at the House of Blues . Photo®Berliner Studio/BEImages



Beck, “Debra”

The Mellow Gold bard turns into a superfreak off the leash. After going for “that burned out in the canyon vibe” of Mutations, Beck revived this live fave as the climax to Midnight Vultures, his tour of Hollywood nightlife. “Debra” is a seductorama slow jam that begins, “I met you at J.C. Penney/I think your name tag said ‘Jenny.’” He invites a special lady to step inside his Hyundai, hitting Spinnerific notes of falsetto ecstasy. “I enjoy toying with masculinity,” Beck explained in Rolling Stone. “Somewhere between Noam Chomsky and Rick James. You’ve got your machismo testosterone on one side, and on the other side, an equally self-involved discovering-the-inner-man-child — the 12th insight of the seventh gate of the 15th threshold to the third golden key to the inner father-child. Those are the extremes. But I guess when you don’t really identify with either of those, you start trying to find out areas where you feel comfortable.”

donell jones

Donell Jones featuring Left Eye, “U Know What’s Up”

Donell Jones rolled out of Chicago with this monster R&B hit, but like everyone else, he was feeling Atlanta: On “U Know What’s Up,” he’s got Left Eye on the mic and a video starring T.I., Big Boi, YoungBloodZ and Usher. Eddie F and Darren Lighty produced the Walkman-melting groove: the first day of summer, Donell out rolling in his Hummer, admiring his crush in her sundress. Left Eye proclaims herself “the Untouchable Girl,” while serving notice that Donell is no scrub.


Ilpo Musto/REX/Shutterstock


Robbie Williams, “Let Me Entertain You”

Britpop harlot Robbie Williams made his big American Invasion move with his expertly titled U.S. debut, The Ego Has Landed. “Let Me Entertain You” is a glam manifesto, channeling Elton John in prime “The Bitch Is Back” candelabra mode. Robbie’s still making headlines for his longtime feud with next-door neighbor Jimmy Page in London. Pagey sued to stop Robbie from building a swimming pool; according to recent accusations, Robbie has been tormenting him by donning a blonde Robert Plant wig and cranking Black Sabbath and Deep Purple at top volume.

kissing book

Kissing Book, “Superman vs. Lloyd”

A three-minute sliver of guitar crushdom, the kind of tune you could randomly hear on the car radio late one night and remember the rest of your life. Kissing Book turned out to be from Portland, led by Andrew Kaffer, whose breathily anonymous voice fits the mood. He sighs about how he once felt like Superman, back when his ex still liked him: “Now I feel more like Lloyd Dobler, driving around at night, trying to figure out where everything went wrong.” The song lilts to the final chorus (“I’m sure you don’t want to hurt me/But you do”), then collapses, with nothing figured out at all.


Moby, “Natural Blues”

When Moby made Play, he was a washed-up techno DJ. He told Rolling Stone, “I was a has-been and I knew I was a has-been.”So he said the hell with it, made a self-indulgent vanity project sampling ancient folk, blues and gospel voices — and fluked into a hit. “Natural Blues” gave a new life to long-dead Alabama singer Vera Hall, after Moby found a 1937 field recording of her spiritual “Trouble So Hard.” In those early-internet times, she was a voice few fans would get a chance to hear, certainly not at the mall or the gym. But in “Natural Blues,” she traveled the earth. As Moby said, “Collage is a place where one plus one equals three.”

dismemberment plan

The Dismemberment Plan, “The City”

The Washington, D.C. band built on the experiments of Fugazi and Rites of Spring for an influential style of verbal nebbish-core neurosis, with Travis Morrison emoting hard over squishy synths and a chopsy rhythm section. The D-Plan hit their stride with Emergency & I, bridging the gap between jazzy experimenters like the Sea and Cake and word-drunk ranters like the Hold Steady and the Mountain Goats. In “The City,” Morrison walks down streets he used to know well, except this place looks dead to him now that she’s gone. The street lamps, the graffiti, the neon lights — it all reminds him of her as he sings, “This is where I live, but I’ve never felt less at home.”

UNITED STATES - JANUARY 01:  NASHVILLE  Photo of Mandy BARNETT  (Photo by Beth Gwinn/Redferns)

Beth Gwinn/Redferns/Getty Images


Mandy Barnett, “The Whispering Wind”

This Tennessee girl came on like the last of the big-time Nashville drama queens, belting country torch ballads fit to make the bartender choke up. “The Whispering Wind” is the song of a woman who’s not afraid to let the mascara run. “Yeah, I like drama,” Barnett told me in 1999. “I just love drama. I need a little turmoil in my life to keep me happy.” She worked with Music Row legend Owen Bradley for her sleeper I’ve Got A Right to Cry, updating the vintage countrypolitan sound of velvety Fifties crooners like Jim Reeves, Eddy Arnold and Patsy Cline. (It was Bradley’s final production.) “The Whispering Wind” is her grand ballad, with sweeping strings, marimba and the ache in Mandy’s voice. (She sang a swell version at Farm Aid.)  She’s made tribute albums to Patsy as well as Don Gibson; last year her ace Strange Conversation took on standards by everyone from Cher to Tom Waits. She’s still got a right to cry.


…And You Will Know Us by the Trail of Dead, “Mistakes and Regrets”

The Austin boys made their rep with an insurrectionary mess they gave the cheeky title Madonna, an album dedicated to the idea that you could not only base your life around Sonic Youth’s Daydream Nation, you could use it to reverse-engineer both punk and prog. The best Trail of Dead show I saw (NYC’s Bowery Ballroom, March 2002) climaxed when they trashed the stage and smashed their instruments — but then realized they still had one more song to play. So they had to sheepishly reassemble their gear and ask the crowd to hand back broken pieces of the drum kit. Nobody could find the pedal, so they pulled a kid onstage to physically kick the bass drum on the one. Somehow it was a beautiful moment.

dressy bessy

Dressy Bessy, “Jenny Come On”

One of the best “Jenny” tunes ever, which is a lofty standard. Tammy Ealon works a bubblegum pop melody in her sugar-sneer, sighing about her girl crush to the garage-band guitars and hand-claps. These Denver kids put the Monkees-worthy “Jenny Come On” on their Kindercore debut Pink Hearts Yellow Moons; they also made the soundtrack of the classic Natasha Lyonne movie But I’m a Cheerleader. Dressy Bessy have a new album this summer, Faster Faster Disaster; they just paid tribute to the late great Pete Shelley with their version of the Buzzcocks’ “What Do I Get?”


Korn, “Freak on a Leash”

Korn heralded a new rap-rock era when bands were all about male angst, DJs, baggy shorts and the letter K. Every afternoon on Total Request Live, “Freak on a Leash” would show up somewhere on the countdown, almost as a protest vote against the rest of the show, with a fan yelling about how the Backstreet Boys and ‘NSync suck, often adding, “Korn rule! Wooooo!” “Freak on a Leash” is nu-metal at its nu-est, with Jonathan Davis reaching into his psychic depths over ultra-violent guitars. “I’ll kiss a dude,” he said. “It means nothing to me because I know I’m straight. I like wearing makeup, I like dressing in girls’ clothes. I was very in touch with my feminine side, and I acted upon it. But in America, it’s bad to be gay. That’s the fucking mentality.”

n sync

‘NSync, “I Drive Myself Crazy”

Lance, JC, Joey, Chris and that other guy — what was his name? Justin something? — blew up big. Everything about NSync was a little loonier than it had to be. (If it’s been a while since you’ve heard “God Must Have Spent a Little More Time on You,” brace yourself for how freaky it sounds now, especially that random triangle “ding!” every few seconds.) “I Drive Myself Crazy” has to be their most underrated hit, an all-too-rare vocal showcase for Chris Kirkpatrick. It could be their before-the-fact answer to Britney’s “You Drive Me Crazy.” In the awesomely offensive video, the boys get locked up in a padded cell at the local insane asylum, mugging in their straitjackets, until a sensual shrink decides to try a little of her one-on-one love therapy on Joey Fatone. NSync tore up hearts with Ariana Grande at Coachella, proving it’s time for a four-man reunion.

shania twain

Shania Twain, “That Don’t Impress Me Much”

Hey, cowboy — is that a 10-gallon hat, or are you just enjoying the show? Shania was a pivotal moment in the evolution of the Global Yeehaw Conspiracy. By 1999, she was the world’s favorite Canadian disco cowgirl; in the U.S., she got marketed as country, but to the rest of the planet, she was a straight-up synth-pop singer. (America was the only place her records got mixed with fiddle and pedal steel.) “That Don’t Impress Me Much” was an international hit — her biggest ever in Europe — with a man-bashing message. Rocket scientists, car aficionados, Brad Pitt, Elvis: none of these poseurs impress Shania. After the end of her marriage to producer Mutt Lange, she fled to the Oprah Winfrey Network for the reality show Why Not? With Shania Twain.

dre snoop

Dr. Dre Featuring Snoop Dogg, “Still D.R.E.”

When Dre finally made it back to the bricks with this single, he was understandably nervous — seven long years after the Chronic, nobody knew if he could do it again. So he made this comeback count, evoking the good old days of the G-Funk Era with Scott Storch’s piano hook. For “Still D.R.E.,” he reteams with his once-and-future homie Snoop Dogg to bring some of that real sticky icky icky. “’95 plus 4 pennies, add that shit up!” Dre also got Jay-Z to ghostwrite his lyrics.

Scottish rock group Mogwai, circa 2001. Left to right: guitarist John Cummings, drummer Martin Bulloch, singer and guitarist Stuart Braithwaite, bassist Dominic Aitchison and guitarist Barry Burns. (Photo by Andy Willsher/Redferns/Getty Images)

Andy Willsher/Redferns/Getty Images


Mogwai, “Stanley Kubrick”

The Glasgow noise lads were on a hot streak in 1999, topping their Come on Die Young album with an even wilder EP: avant-loud guitar freakery with an air of boozy mischief. “I think people in the audience should wear earplugs,” guitarist Stuart Braithwaite told Rolling Stone. “The point of the volume is to feel your body being shaken.” (Anyone who goes to a Mogwai gig without earplugs is insane, then or now.) When asked the difference between Mogwai and prog, Braithwaite replied, “Capes.” “Stanley Kubrick” captures Mogwai right around the time Stephen Malkmus was calling them “the best band of the 21st Century.” It’s a dreamy sound — digitally warped guitar fuzz, organ, meditative drums, low-volume radio voices drifting through the static. At this point, Mogwai might be the longest-running guitar band that’s never made a bad record. (Even the one they called Rave Tapes has its moments.) Here’s to their next 20 years.


Takako Minekawa, “Plash”

The Japanese synth mastermind was one of the most dazzling artists to emerge from Tokyo’s shibuya-kei scene, along with fellow boho-techno eccentrics like Buffalo Daughter, Kahimi Karie and Cornelius. She was originally in the band Fancy Face Groovy Name, but Takako Minekawa always had her own style. In gems like Cloudy Cloud Calculator, Roomic Cube and Fun9, she cut her electro exploits with vintage lounge pop, big on lyrics about cats and spiders. (On one of her records, she did an outlandish desecration of the Tornados’ 1963 space-age instrumental, “Telstar.”) “Plash” turns a Brazilian bossa nova guitar loop into fractured funk; in the video, she sings into a hairbrush and then brushes her hair with it. Minekawa keeps making adventurous experiments, collaborating with guitarist Dustin Wong on recent records like the excellent 2017 Are Euphoria.


Stephen Sweet/REX/Shutterstock


Wilco, “Via Chicago”

Wilco broke out of the country-rock pigeonhole for good on Summerteeth, as Jeff Tweedy and Jay Bennett flipped out into their druggiest studio experiments, with nobody around to slap them out of it. As drummer Ken Coomer recalled in Greg Kot’s Wilco history, “There wasn’t really a band, just two guys losing their minds in the studio.” “Via Chicago” was a major step forward for Wilco, reaching for the widescreen scale of Yankee Hotel Foxtrot and A Ghost Is Born. It starts out as a dark acoustic murder ballad (“I dreamed about killing you again last night / And it felt all right to me”) before going off the rails with ornate synths and guitar feedback. At the end, Tweedy croaks, “I’m comin’ home, I’m comin’ home,” but he sounds more lost than when he began.

rilo kiley

Rilo Kiley, “The Frug”

The first glimmer of greatness from Jenny Lewis and crew, hidden on the soundtrack of a Christina Ricci flick nobody saw. (Desert Blue, it was called). Lewis sings about a hopeful crush, the kind where the talking leads to touching but the touching doesn’t lead to sex yet, doing old-school teen dances like the Freddie and the Smurf. I only heard “The Frug” because MTV played it exactly once, late on a Sunday night, at the butt-end of 120 Minutes. I bought the soundtrack the next day, put “The Frug” on mix tapes all summer, raved about it in Rolling Stone, and wondered if this band with the funny name — “Rilo Kiley”? — might have any other songs this sharp. But this was just the first of their many takeoffs and landings. Jenny Lewis just released her stellar On the Line, which puts her in the gratifyingly crowded class of artists on this list who are still thriving in 2019, alongside Stephen Malkmus and the Backstreet Boys.

elf power

Elf Power, “Jane”

Why do songs about women named Jane always rule? Unless they’re by Maroon 5? Elf Power came up with one of the very best “Jane” songs ever, if you can forgive a band for calling itself “Elf Power,” which admittedly might be a stretch. This Athens G-A combo dropped A Dream of Sound, from the Elephant 6 collective that also produced Neutral Milk Hotel, Olivia Tremor Control and Of Montreal. “Jane” is a woozy love song with Kinks-ish guitar chime and a very Zombies trumpet hook, singing about a deep girl who can’t be figured out, living alone with the visions in her head.

christina aguilera

Christina Aguilera, “Genie in a Bottle”

The year was full of Mickey Mouse Club power kids taking over: Xtina arrived in the wake of Britney and Justin and JC. Her debut hit “Genie in a Bottle” was the best hit about sticky fingers since Billy Squier’s “The Stroke,” as she pleaded to be rubbed the right way. From the start, Aguilera was more into rubbing Mariah-style ballads than dance tracks like this one, but “Genie in a Bottle” was a foretaste of her “Dirrty” assless-chaps phase. You gotta make a big impression. You gotta love what you do.




DMX, “It’s All Good”

The Ruffest of all Ryders. DMX had the year’s queasiest album art with the gore-spattered mess of his horrorcore statement Flesh of My Flesh, Blood of My Blood, where he proved himself the only rapper who could throw down with both Marilyn Manson and Mary J. Blige. The Dog humps the world’s leg in “It’s All Good,” espousing a simple philosophy: “It’s all good, it’s all right / Fuck all day, fuck all night.” Theoretically that schedule wouldn’t leave much time for criminal activity, but DMX is quite the multitasker. “It’s All Good” is his pro-bitch statement (“I like ‘em greedy / Black like Idi”) over a vintage disco “Heartbeat” bassline. Bonus points for the liner notes: “To my fans…Your love is like food for a starving DOG.” Good news: DMX just got back on the streets as a free man, after serving a year in prison for tax fraud.

John Prine performing at Town Hall on Thursday night, September 16, 1999.(Photo by Hiroyuki Ito/Getty Images)

Hiroyuki Ito/Getty Images


John Prine, “In Spite of Ourselves”

The legendary folkie songwriter was still recovering from a near-fatal bout of throat cancer when he sang “In Spite of Ourselves.” George Strait just had a country hit with his version of “I Just Want to Dance With You,” which is how Prine paid his hospital bills. His protegée Iris DeMent joins him on this duet to middle-aged love and lust, which Prine wrote for his wife: “In spite of ourselves we’ll end up sittin’ on a rainbow / Against all odds, honey, we’re the big door prize.” You can hear the chemo in his gravelly drawl; you can also hear the cocky grin of a guy who feels like the the luckiest bastard alive. Still rolling in his seventuies, Prine just released one of his best albums last year, the acclaimed The Tree of Forgiveness.


Stephanie Paschal/REX/Shutterstock


Sleep, “Jerusalem”

The stoner-doom metal pioneers reached new levels of heavy with “Jerusalem,” an hour-long dirge with the opening line, “Drop out of life with bong in hand!” “When we started, we were smoking lots of pot and taking acid, and the soundtrack to all of our fucking lives at the time was essentially Black Sabbath,” bassist Al Cisneros told Rolling Stone‘s Kory Grow last year. “Our entire universe was Black Sabbath. We couldn’t understand why the bands that we didn’t like were playing so fast.”

The San Jose trio spent four years writing the song that became “Jerusalem; they refined it into Dopesmoker, released a few years later. It tore them apart: Cisneros and drummer Chris Hakius went on to Om, while guitarist Matt Pike formed High on Fire. But the legend of “Jerusalem” has just grown. Last year Sleep dropped their comeback The Sciences on (when else) 4/20. The inspiration? “Weed and science fiction, kind of like always.”

paul mccartney

Paul McCartney, “No Other Baby”

Macca at his most emotionally unguarded. He’d just lost Linda to cancer, after 30 years when they were inseparable — they never spent a night apart until the week he went to prison. Deep in his grief, he went back into Abbey Road to make Run Devil Run, a set of oldies by his Fifties rock & roll heroes: Chuck Berry, Fats Domino, Wanda Jackson, (of course) Elvis. But the show-stopper is “No Other Baby,” a long-forgotten 1958 side by the obscure U.K. skiffle group the Vipers. Paul turns it into an elegiac haiku for Linda, with sparse guitar from Pink Floyd’s David Gilmour. He does what John Lennon merely attempted on Rock & Roll, reviving the songs they loved together growing up in Liverpool — but he gives it all the raw passion of Plastic Ono Band. “No Other Baby” is a tribute to the life he shared with Linda. And maybe also the life he shared with John, George and Ringo.


Blaque, “808”

Three Atlanta R&B girls in a steam bath of sex-mystic soul, singing about how the beat of love goes boom like the drum machine in your heart. Blaque spent most of 1999 on tour opening for their mentors TLC; they had a cameo as cheerleaders threatening to kick Kirsten Dunst’s ass in Bring It On. Their name stood for “Believing in Life and Achieving a Quest for Unity in Everything.”


(MANDATORY CREDIT Ebet Roberts/Getty Images) UNITED STATES - JANUARY 01:  Photo of LUNA; Stanley Demeski, Dean Wareham, Sean Eden  (Photo by Ebet Roberts/Redferns)

Ebet Roberts/Getty Images


Luna, “Math Wiz”

New York guitar aesthetes Luna spent the decade making one brilliant dream-pop record after another, to the point where they made everyone else in the rock game look a little thick. Dean Wareham spun his tales of romantic obsessives getting swallowed up in the big city, while he and Sean Eden revved their sleek guitars. “Math Wiz” is a riddle of a song, from their fifth album, The Days of Our Nights: Wareham worries about his insomnia, but that just makes it worse. Luna were always out of step with the times — elegant when people wanted rough, wry when people wanted earnest. But every album they made holds up to literally hundreds of listens. (Penthouse and Pup Tent must be well into five digits in my apartment.) They still bring it onstage, too — the longer the guitar solos, the better the Luna show.

mary j blige

Mary J. Blige, featuring Elton John, “Deep Inside”

The Queen of Hip-hop Soul gets realer than ever on “Deep Inside,” from her gem Mary. She opens up about mid-life loneliness, wishing for a friend or lover she can trust, with only her lavish lifestyle to console her. Tell it, Mary: “The car I drive, the clothes I wear, the diamonds, the furs, the house don’t make the woman.” It’s lonely at the top. Like so many of us, Mary turns to Elton John to help her figure it all out, singing over a piano sample from “Bennie and the Jets.” “Deep inside I wish that they could see, that I’m just plain old Mary” — but there’s nothing plain about this woman.

English electronic musician and composer Aphex Twin (Richard James), circa 2000. (Photo by Andy Willsher/Redferns/Getty Images)

Andy Willsher/Redferns/Getty Images


Aphex Twin, “Windowlicker”

Richard D. James managed to invade the hit parade with “Windowlicker,” a six-minute ambient mind-freak jigsaw that somehow reached Number 16 on the U.K. singles chart. It was a historic high-water mark for the “ordinary people listening to techno between Oasis and TLC and Puffy and nobody had a problem with that” era. (He also made a comedy promo clip that hardly featured the actual music; it’s fair to say the song has outlasted the video.) By his own Aphex Twin standards, “Windowlicker” is downright linear, with that three-note synth refrain. Yet it’s also harsh, uncompromised, perverse — a mix of drum-and-bass textures, shattered-glass crashes, sex grunts, ending with a solid minute of dentist-drill white noise.

The Magnetic Fields

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The Magnetic Fields, “The Luckiest Guy on the Lower East Side”

Stephin Merritt’s three-disc tour de force 69 Love Songs seemed to drop out of nowhere — even fans didn’t see this coming. He’d already crafted so many elaborately clever song cycles with the Magnetic Fields, Future Bible Heroes and the 6ths. (Their 1995 Wasps’ Nests is a real spinner, especially when Barbara Manning sings “San Diego Zoo.”) But on 69 Love Songs, the sentimental fave has to be “The Luckiest Guy on the Lower East Side,” a Sesame Street-ready jingle where he cruises the city streets with ukulele, toy piano and Gerry Goffin-style wordplay. When singer Dudley Klute hits that 14-second high note at the end, he sounds ecstatic and bored — the ultimate Stephen Merritt combination.


Eminem, “My Name Is”

“Hi, kids! Do you like violence? Wanna see me stick Nine Inch Nails through each one of my eyelids?” Over Dr. Dre’s cartoon funk, Marshall Mathers grabs the mic in “My Name Is,” his first and truest incarnation: the shock comic as teenage trailer-park loser, picked on at school and work. (As he put it elsewhere on The Slim Shady LP, “Class-clown freshman / Dressed like Les Nessman.”) In “My Name Is,” he’s a rap nobody whose career highlight is getting asked for an autograph at White Castle: “Dear Dave, thanks for the support, asshole.”

ricky martin

Ricky Martin, “Livin’ la Vida Loca”

Chris Rock hosted the MTV Video Music Awards on 9/9/99 — the decade’s peak celebrity bitchfest, hands down — and famously tagged Ricky Martin “the Puerto Rican Al B. Sure.” The former Menudo stud shook his bon-bon to the electric-salsa sleaze of “Livin’ la Vida Loca,” falling under the spell of a mocha seductress with devil-red lips. (Does she bang? She bangs.) He also earned a shout-out in Sisqo’s “Thong Song.” Ricky’s popularity took a dive after his disastrous dance with President George W. Bush at the Lincoln Memorial inaugural celebration, but he hung in there, eventually came out and earned long-overdue redemption last year playing the bereaved boyfriend in American Crime Story: The Assassination of Gianni Versace. This year, he kicked off the Grammy ceremony — 20 years after the night he stole the show.

big tymers bg bling

B.G., featuring Lil Wayne, Turk, Juvenile & Big Tymers, “Bling Bling”

The planet gets a dose of Lil Wayne — nothing was ever the same. “Bling Bling” was a massive shot out of New Orleans, with that Mannie Fresh electro-twerk production and boasts from Weezy, Birdman, Lil Turk and Juvenile to announce the Cash Money era, declaring, “1999 and it’s our time to shine!” Everybody gets a chance to articulate the Cash Money code of life, from partying (“The Cash Money motto is to drink until we throw up” — OK then) to home video equipment. “Twenty-inch TV is a must” — that was plenty in 1999. This song single-handedly turned the Hot Boyz hook “bling bling” into a catchphrase beloved by Middle American moms. But even in this early stage, Weezy stood out from the
crowd—sessions started at 4 p.m. because he was still in school. “Wayne was so slick,” Juvenile just told Rolling Stone’s Charles Holmes. “Wayne would listen to all our shit and go in the fucking corner. Nigga come back with some brrrrt sound effects and brrrrrp blinging all. I said, ‘Man.’”

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