ItsNotYouItsMe Throwback Features 99 Grooviest Songs of 1999!

ItsNotYouItsMe Throwback features 99 grooviest songs of 1999!

"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.

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, “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, “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, “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 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, “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, “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, 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, “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 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.”

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, “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 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.

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 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.

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, “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.”

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.”

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, “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.”

‘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, “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.

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.

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.

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, “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, “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, “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, “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.

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, “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.”

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, 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.

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, “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, “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.

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.’”

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, “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.

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.

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 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.

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.

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.

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.”

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.”

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.

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.

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 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.

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.

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.

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.”

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.

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.

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.

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.”

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.

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, “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.”

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.

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, “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.

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, “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.

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, “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.”

Mandy Moore, “Candy”

You know who you are. Your love’s as sweet as candy. I’ll be forever yours. Love always, Mandy.

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”

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, “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.

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.

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!”

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.

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!”

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.

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.

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, “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, “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, “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 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, “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, “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”

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”

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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