At the end of the millennium, popular music was behaving like we really might only have one year left. You’d be hard pressed to find another year in pop history that tried to cram more stuff into 12 months: Breakthroughs, comebacks, crossovers, last gasps. Career-defining smashes that still rank among the most-karaoked songs nationwide. Bizarro one-offs that wouldn’t make sense for another decade, until Twitter was invented to give them proper context. The Vengaboys. Truly, 1999 had it all.
It’d take far more than 99 songs to summarize everything that the final year of the 20th century had to offer musically. But below, Billboard counts down our 99 favorites from the peak of turn-of-the-millennium megapop, an era of such robust sales that the RIAA had to introduce a new level of certification to account for all the new blockbusters, an era of such blinding star power that we needed Carson Daly’s assistance to establish a proper hierarchy. It’s time to praise ’em like we should.
First, though, a note about eligibility: Songs were counted as eligible if they were released as singles in ’99, or if they debuted on the Billboard charts in ’99. But if they didn’t hit the Hot 100 until the next year, or if they debuted in ’99 but didn’t hit No. 1 until the year after, we’re counting ’em for ’00. So apologies to “Say My Name,” “What a Girl Wants,” “Maria Maria” and several others — we’ll probably see them on this list next year.
See our list below — with a Spotify playlist of all the songs at the bottom — and look out for more content from the year that brought Kenny G back to the Hot 100 all week on Billboard.com.
99. Sarah McLachlan, “I Will Remember You” (Live) (No. 14, Hot 100)
The lyrics to Sarah McLachlan’s gently timeless piano ballad — a surprise hit off her live Mirrorball set, four years after its initial debut on the Brothers McMullen soundtrack — so perfectly capture the concept of saying “so long” and moving on that one can’t hear it without visualizing a montage of playing behind it. Over time, it’s become a staple at mile-marker events, from campfire sing-alongs to send offs of any sort — meaning that in an ironic twist, “Remember” very well could now be an ode to itself. — LYNDSEY HAVENS
98. Maxwell, “Fortunate” (No. 4, Hot 100)
Songwriter and producer R. Kelly says he persuaded Maxwell to drop his ambition to record the Life soundtrack’s title cut in favor of this quiet storm jam — and we are all better for it. If fans of the neo-soul prince’s first album Maxwell’s Urban Hang Suite thought sophomore LP Embrya lacked direction, “Fortunate” steadied the course, as a swooping falsetto run bursts forth seconds after pressing play, and envelops the listener in a lush, intimate vocal verse. But the song hangs on its unique one-word title to simply and completely describe the mood Maxwell creates: Plenty of singers have been “blessed” or “lucky” throughout pop history; only one remains fortunate. — TREVOR ANDERSON
97. Limp Bizkit, “Nookie” (No. 80, Hot 100)
Let’s face it: the nu-metal era that rattled the late ‘90s and early ‘00s was weird as hell. But 20 years ago, the oft-maligned genre feels more like a refreshing shift that cleared out the last remaining vestiges of grunge — thanks to smashes like Limp Bizkit’s “Nookie.” Lifted from the band’s sophomore album Significant Other, the single showcased frontman Fred Durst’s petty misogyny, not-so-tightly concealed by the obnoxiously undeniable groove. That chauvinistic streak still hasn’t broken in popular music to this day, but unfortunately that’s the way the cookie crumbles. — BIANCA GRACIE
96. Blur, “Coffee & TV” (Did not chart)
Two years after crashing American shores with a grunge send-up potent enough to become a Jock Jam perennial, Blur scored their last major hit of the millennium with a mid-tempo strummer so jaunty and precious it wouldn’t sound out of place on a Belle & Sebastian album. The song may have been all about the soul-crushing banality of living the quiet life — guitarist Graham Coxon, in a frontman cameo here, had recently gone sober — but its infectiousness is a vice unto itself, and the milk-carton odyssey that served as its video accompaniment was adorable enough to even leave A.J.. Soprano enraptured. — ANDREW UNTERBERGER
95. S Club 7, “S Club Party” (Did not chart)
The seven-member British pop group made sure they’d be remembered 20 years later with a song that not only gets the party going, but serves as the perfect introduction to its hosts. While 13 S Club references — as well as an entire bridge dedicated to shouting out each individual member — could come off as self-involved, the unshakeable melodies and singalong chants in “S Club Party” were appropriately convincing 20 years ago that there really ain’t no party like an S Club party. — TAYLOR WEATHERBY
94. Foxy Brown, “Hot Spot” (No. 91, Hot 100)
The low chart showing of “Hot Spot” doesn’t do it justice — this song, from the rapper’s Billboard 200-topping second album Chyna Doll, still slaps. Brown co-wrote the banger with Jay-Z, and together they set flexes like “My coat is ostrich, flow is the hottest/ You ain’t got dough, you can’t go with the Fox bitch” to a bright and scratchy beat from producers Irv Gotti (of Murder Inc. fame) and Lil Rob. After securing big features (Blackstreet, Dru Hill, Jay himself) for each of her Ill Na Na singles, “Hot Spot” was the first solo single for Brown — but when she closes out the chorus with “This is our world, me and my girls,” the track changes to a crew cut, a perfect ladies’ night anthem. — CHRISTINE WERTHMAN
93. The Get Up Kids, “Ten Minutes” (Did not chart)
You could argue 1999 was the last year emo was completely underground: Dashboard Confessional hadn’t yet debuted and Jimmy Eat World’s Bleed American was still two years away. But if you were pitching a trend piece on the genre’s ascendance in 1999 — the year Seventeen printed its now-Internet-famous How-To-Emo guide — you were most definitely highlighting Kansas City’s Get Up Kids, who’d released their magnum opus Something To Write Home About that fall, with “Ten Minutes” its hooky centerpiece. The band added keyboardist James Dewees after its scrappier original recording (for the Sub Pop singles series in early ’99) and his swirling synthesizers on the album version push co-frontman Jim Suptic’s brink-of-a-breakdown choruses to power-pop glory. — CHRIS PAYNE
92. Dead Prez, “Hip Hop” (No. 49, Rap Songs)
Immortalized as the low end-heavy intro music for the title star on Chappelle’s Show, Florida-New York duo dead prez’ signature single “Hip Hop” has aged beautifully. For a song that’s broadly remembered as a bitter jeremiad, the perspective offered by MCs Stic.man and M-1 is actually pretty magnanimous — in the first verse, M-1 promotes honesty and the belief that the system of listeners will regulate the bullshit: “If you a liar-liar, pants on fire, wolf-crier, agent with a wire/ I’m gon’ know it when I play it.” Of course, that it’s aged well means that everything still applies, in particular Stic.man’s sobering final lines: “I just stay awake/ This real hip-hop, and it don’t stop ’til we get the po-po off the block.” — ROSS SCARANO
91. Brandy, “Almost Doesn’t Count” (No. 16, Hot 100)
By the spring of 1999, Brandy was riding high on the momentum of a combined 15 weeks atop the Billboard Hot 100 with “The Boy Is Mine” and “Have You Ever.” But “Almost Doesn’t Count,” fifth single off her blockbuster Never Say Never set, finds the then-20-year-old multi-hyphenate giving a more nuanced take on a failed relationship. While she remains heartbroken by her ex’s “funny hesitation of a heart that’s never really sure,” her laid-back vocal and repetitive lyrics over solemn strumming imply a wisdom that teeters on damning judgment, perceptive enough to walk away from his half-empty promises. — ERIC FRANKENBERG
90. No Doubt, “New” (No. 7, Alternative Songs)
The 1999 cult classic flick Go delivered two things for Anaheim ska-punk stars No Doubt: another alt-rock top 10 hit and a seismic stylistic shift. “New” was the group’s contribution to the movie’s soundtrack, a standalone single that marked a stopgap between 1995’s eventually Diamond-certified breakthrough LP Tragic Kingdom and their fourth album, 2000’s Return to Saturn. Like any great No Doubt song, it’s got a chorus that can only sound good when Stefani howls it, but it’s the inventive, synth-spackled instrumentation that revealed inklings of the new wave experimentation we’d see in the next year’s “Simple Kind of Life” and beyond. In short: “New” wasn’t just new, but a harbinger of things to come. — HILARY HUGHES
89. 112 feat. Lil Zane, “Anywhere” (No. 15, Hot 100)
Aside from maybe Ginuwine’s “Pony,” you won’t find a late-’90s R&B cut that hits quite as hard as the unmistakable first note of “Anywhere,” 112’s ode to getting down whenever and wherever the mood strikes. Contained in that one beat is the promise of something sexy, playful and maybe even a little dirty (OK, a lot dirty), and the silky-smooth lead vocals of Slim and Q deliver just that — even managing to make the outdated and impractical suggestion of a waterbed scenario still sound like a desirable option. — KATIE ATKINSON
88. B*Witched, “C’est La Vie” (No. 9, Hot 100)
Why on earth would a song open with two members of a girl group bantering incredulously about whether one resembles her father? Maybe to throw off the trail of a song that’s loaded with a surprising amount of double-entendres. It’s like the Irish quartet — all credited here as songwriters — saw all the innuendos the Spice Girls snuck into their songs in years prior and took it as a challenge to outdo them. Come on: I’ll show you mine if you show me yours. I’ll huff, I’ll puff, I’ll blow you away. Do you okay with the girls, do you play with the boys? The breezy, nursery-rhyme quality of the chorus is only half of what makes the song such enduring ear candy — the rest is the intangible thrill that comes from knowing you’re getting away with something. — NOLAN FEENEY
87. Aimee Mann, “Save Me” (Did not chart)
After “Voices Carry” hitmakers ‘Til Tuesday broke up in the late ’80s, frontwoman Aimee Mann went solo as a singer-songwriter — earning her critical acclaim, as well as a fan who would introduce her to a new generation of listeners at the end of the century: Paul Thomas Anderson. The director used Mann’s music in his ensemble melodrama Magnolia, for which Mann wrote “Save Me,” a dryly humorous (though not insincere) request for a savior. “You look like a perfect fit/ For a girl in need of a tourniquet,” Mann sings alongside ambling acoustic guitar. “But can you save me?/ Come on and save me.” It’s a simple plea, but the straightforwardness of the request gives it a weight that will knock the wind out of you. — C.W.
86. Kenny Chesney, “She Thinks My Tractor’s Sexy” (No. 74, Hot 100)
Before Florida Georgia Line went for a cruise or Luke Bryan asked a girl to shake it for him, Kenny Chesney changed the course of country by touting the power of his farm equipment. Chesney’s “She Thinks My Tractor’s Sexy” eventually paved the way for FGL, Bryan, Jason Aldean and more as the progenitor of Bro Country, but back in ’99, Chesney’s song exuded a more laid-back and winking approach to love and women, never assuming that it would come to grow into the genre’s most dominant ethos. — DENISE WARNER
85. Filter, “Take a Picture” (No. 12, Hot 100)
There would have been no ’90s rock one-hit wonder more predictable than Filter, a post-grunge industrial rock success story thanks to 1995’s oft-misinterpreted screamer “Hey Man, Nice Shot.” But though 1999’s Title of Record led with the ignorable alt-metal of first single “Welcome to the Fold,” it held a secret weapon in reserve: “Take a Picture,” a dreamy stomper about being a drunken ass on an airplane. The song’s invigorating acoustic chug and languid singalong chorus (“Could you take my picture/ ‘Cause I won’t remember”) allowed it to cross over to top 40, but its shouted late-song climax (“HEY DAD, WHADDYA THINK ABOUT YOUR SON NOW??“) is as blood-curdling as anything from “Nice Shot.” — A.U.
84. Busta Rhymes, “Gimme Some More” (No. 24, R&B/Hip-Hop Songs)
Over a sample of the disorienting, uneasy strings from Bernard Herrmann’s “Prelude (Psycho Theme),” Busta mumbles about bumping his head as a kid, before the stuttering beat skips in and the rapper’s inimitable, voluble rasp takes off at breakneck speed. The song never quite reaches the fever pitch it threatens to, leaving the listener as on-edge as Janet Leigh driving down the highway, perpetually looking over her shoulder and waiting for the other shoe to drop. — JOE LYNCH
83. Marc Anthony, “I Need to Know” (No. 3, Hot 100)
This punchy, percussive song sits at the precise midpoint between American and Latin pop, so it’s fitting that it was a smash in both English and Spanish (as “Dímelo”). Anthony’s repeated references to his “baby girl” aren’t especially woke, but how many of us were woke in 1999? One thing’s for sure: No one ever heard this song and wondered what the title was, as Anthony repeats the title phrase over 30 times. In his defense, sometimes you really do need to know. — PAUL GREIN
82. Orgy, “Blue Monday” (No. 56, Hot 100)
The best cover songs not only riff on the original’s sound and presentation, but unlock a previously unnoticed element within the song itself, something hiding in plain sight. Orgy’s industrial-rock take on New Order’s synth-pop classic snips away some of the original’s four-on-the-floor propulsion in favor of the brute force of crushing guitars, but the lyric “How does it feel, to treat me like you do?” morphing from a sniping lament into a pissed-off howl of a refrain is surprisingly effective. New Order’s “Blue Monday” is still the best “Blue Monday,” but Orgy made it a lot closer than one might have predicted. — JASON LIPSHUTZ
81. *NSYNC, “I Drive Myself Crazy” (No. 67, Hot 100)
The final single from *NSYNC’s self-titled debut album, “I Drive Myself Crazy” is as easy listening as the group got — down to Chris Kirkpatrick (not Justin Timberlake or JC Chasez) stepping into the spotlight to nail the opening verse. While the lovely quasi-power ballad wasn’t a chart-topper, the music video became a TRL staple as a perfect snapshot of the period’s pop culture: Elisa Donovan, who played Amber in 1995’s Clueless, even makes a cameo as Joey Fatone’s jilted girlfriend. While the mental health imagery parodied in the clip feels questionable at best 20 years later, the song definitely stands the test of time. — BECKY KAMINSKY
80. Armand Van Helden feat. Duane Harden, “You Don’t Know Me” (No. 2, Dance Club Songs)
“You Don’t Know Me” is a dance music Frankenstein: a chimera of sampled ’70s disco strings, early ’90s house drums (also sampled), and the powerhouse vocals of German-American singer Duane Harden. The combination was so potent that it reached No. 2 on Billboard’s Hot Dance Music/Club Play listing, and even knocked the Offspring’s “Pretty Fly (For a White Guy)” off the top of the U.K. charts. — HARLEY BROWN
79. B.G. feat. Baby, Turk, Mannie Fresh, Juvenile & Lil Wayne, “Bling Bling” (No. 36, Hot 100)
Before Lil Wayne morphed into a rap juggernaut, he and his Cash Money cohorts ushered in a new catchphrase that would later find a home in Merriam-Webster: “Bling Bling.” Driven by a chirping Mannie Fresh beat, the song became a top 40 hit, while the indelible video (headlined by B.G.) taught everyday folk infinite ways to stunt. Commercials, movies and even regular Joes adopted the cheeky catchphrase, in hopes of dripping in swag. Though the phrase doesn’t gleam as much as it once did, you still can’t deny the song’s luster each time it comes on. — CARL LAMARRE
78. Ginuwine, “So Anxious” (No. 16, Hot 100)
Despite the title, there’s nothing shy about Elgin Baylor Lumpkin’s turn-of-the-century classic. With Static Major penning the words and Timbaland manning the boards, “Anxious” already had the recipe for success, but Ginuwine adds the key ingredient with his upper register, especially when his honey-dripped falsetto skips along that extended “soooooo anxious” on each chorus. Maybe “Anxious” wasn’t a game-changer along the lines of previous Ginuwine-Major-Timbaland combo “Pony,” but it offers up everything we love about grown-and-sexy R&B. — T.A.
77. Donell Jones feat. Lisa “Left Eye” Lopes, “U Know What’s Up” (No. 7, Hot 100)
The horny ode to the sundress — it’s a special microgenre in which a Drake x Kendrick collab and a beloved Earl Sweatshirt tweet are canon. Donell Jones’s “U Know What’s Up” is a proud member of this lineage, evoking the power of the garment through the beautiful first day of summer, chromed-out Hummers and exposed thighs. But even if you’re not paying attention to the lyrics behind the sticky vibe of the hook, the bounce of Eddie F. and Darren Light’s production lets you know what we’re talking about. — R.S.
76. System of a Down, “Sugar” (No. 28, Mainstream Rock)
In no way, shape or form could eventual alt-metal sensations System of a Down have picked a better single out of the gate than “Sugar.” In addition to capturing the raucous, no-holds-barred energy of their early live shows, the song contained much of the Armenian American rockers’ DNA — pummeling staccato riffing, shifts between singing and guttural screams, whiplash-inducing tempo changes — in one two-and-a-half-minute serving. At the onset of nu metal’s multi-year hold on mainstream rock, “Sugar” showed that the genre had more than a few tricks up its sleeve. — KEVIN RUTHERFORD
75. D’Angelo feat. Method Man and Redman, “Left and Right” (No. 70, Hot 100)
On paper, the pairing of the silky-smooth D’Angelo with hip-hop’s resident stoners Method Man and Redman may have seemed like an odd choice — but when it comes to effortless virtuosity, there were few who could swagger through a track like that trio does on “Left and Right.” The Voodoo single doesn’t quite kick off so much as ease in, with all three vocalists playing off each other in a way that can’t be drawn up in the lab, but works perfectly through pure chemistry. — DAN RYS
74. Monica, “Angel of Mine” (No. 1, Hot 100)
“Angel of Mine,” a top ten hit overseas for U.K. girl group Eternal, was just too damn endearing a musical mash note to not eventually make it to young lovebirds stateside, as it finally did with Monica’s third straight Hot 100 No. 1 hit. Anyway, the mid-tempo love song deserved having a performer as winning as the then-18-year-old R&B star to deliver its sighing lyric, which displays a Smokey Robinson-like skill at conveying universes of emotion and truth in the simplest wording possible: “I look at you, looking at me/ Now I know why they say the best things are free.” — A.U.
73. Mobb Deep feat. Lil Kim, “Quiet Storm” (Remix) (No. 17, Rap Songs)
When thinking about quiet storm, your mind drifts to memories of driving home during a rainy Sunday evening while jamming to lovelorn R&B ballads on the radio. But in true hip-hop fashion, Mobb Deep decided to flip that concept to create a chilling club anthem. With a practically subsonic bass lift from a Grandmaster Flash classic and the inspired addition of Lil Kim on the remix (who gives us one of her most immaculate verses to date), the Queensbridge legends set a precedent for future rappers to mix their spitting about popping bottles with a splash of somber reflection. — B.G.
72. 702, “Where My Girls At” (No. 4, Hot 100)
Las Vegas trio 702 took this Missy Elliott-penned tune and turned it into one of the standout ladies’ anthems of the turn of the millennium, alongside classics by groups like Destiny’s Child and TLC, the latter of whom rejected this very song. Though the verses aren’t as commanding as those other megahits, “Girls” boasts an infectious chorus that no matter where you are — in the club, the car or the crib — once it starts, you know you’re booked for the next 20 seconds of your life. — T.A.
71. Rage Against the Machine, “Guerrilla Radio” (No. 69, Hot 100)
L.A. funk-metal paragons Rage Against the Machine spent nearly a decade soapboxing for a social justice revolution before they lit a fuse on the scorching “Guerrilla Radio,” the lead single from career-defining manifesto The Battle of Los Angeles. Its adrenaline-pumping call to arms was adopted by both the masses and the establishment, from the legion of gamers who found the perfect skate track on the Tony Hawk’s Pro Skater 2 soundtrack, to the Recording Academy voters who awarded it the Grammy for best hard rock performance in 2001. — BRYAN KRESS
70. H.O.T., “I Yah!” (Did not chart)
Considered the first K-pop idol group, H.O.T.’s 1999 hit “I Yah!” was one of the boy band’s most successful hits. A song fueled by rage, it’s dominated by smooth orchestral instrumentals that clash with a dramatic infusion of metal and hard rock elements, via its wailing guitar riffs and screaming vocals. Released along with a music video that drew on Japan’s visual kei scene for inspiration, the group took the opportunity to call out corruption in society, and created an anthem describing the frustrations of the current generation of youth. It was inspired by a tragedy the previous June, when unsafe conditions at a camp brought about by bribery resulted in over a dozen young children dead in a fire. — TAMAR HERMAN
69. Moby, “Bodyrock” (No. 6, Dance Club Songs)
There are more ambitious tracks than “Bodyrock” on Moby’s 1999 breakout masterpiece Play — but “Bodyrock,” with its jagged Gang of Four-inspired guitar runs and Spoonie Gee samples, captures Moby’s genius as a dance artist. Perhaps the song does bear a resemblance to Fatboy Slim’s work — which was an initial criticism — but Slim’s hits from that time never achieve the same euphoric release the Herman Melville descendant produces here. As the spazztastic official video for the song demonstrates, “Bodyrock” is a song meant for letting one’s freak flag fly, flap or convulse. — FRANK DIGIACOMO
68. Black Star feat. Common, “Respiration” (No. 54, R&B/Hip-Hop Songs)
Mos Def and Talib Kweli Are Black Star was a grand introduction for both Brooklyn rappers, released Sept. 29, 1998. But its second single, the Common-assisted “Respiration,” crept onto the Hot R&B/Hip-Hop Songs chart six months later, paying tribute to the relentless grit of the city that raised them, while also grappling with the ways it has shaped them. “Respiration” is the last single Black Star released, but the vague promise of new music lingers tantalizingly 20 years later. — E.F.
67. TLC, “Unpretty” (No. 1, Hot 100)
TLC (Tionne “T-Boz” Watkins, Lisa “Left Eye” Lopes and Rozonda “Chilli” Thomas) were one of the most empowering girl groups of the ‘90s, inspiring women of all ages around the world with their unapologetic lyrics. In 1999, the group scored their second straight Hot 100 No. 1 hit from their album FanMail with the alt-rock-influenced “Unpretty,” tackling the issue of insecurities and sending the important message of self-worth and self-love. Twenty years later, this hit continues to emphasize that not even all the hair extensions, plastic surgery and makeup in the world can buy true beauty, and that women should never feel obliged to meet such unrealistic physical standards anyway. — JESSICA ROIZ
66. Wilco, “A Shot in the Arm” (Did not chart)
A drug jam from one of our most barred-up songwriters, Jeff Tweedy. “The ashtray says you’ve been up all night” is clever, novel, evocative: a line so good you’re not mad that he repeats it. The song is driven by repetition, like a habit, like a junkie. The climax — where the Wilco frontman gradually warms up to his plan to get a fix, and then finally depresses the plunger, while the synths go dissonant and he’s shouting himself hoarse (“something in my veins, bloodier than blood”) — is so potent, it feels like it should be the end. It’s a neat trick, making you forget the harrowing comedown: “What you once were isn’t what you want to be any more.” — R.S.
65. Garbage, “Special” (No. 52, Hot 100)
Lead singer Shirley Manson’s pen is just as lethal as her royal fighter pilot counterpart in the visual for Garbage’s sultry-yet-propulsive single “Special.” She dismantles an unrequited connection with excruciating directness (“Now you’re here and begging for a chance/ There’s no way in hell I’d take you back”), over a rush of competing sounds from percussionist and producer Butch Vig’s pioneering, electronic-influenced studio experimentation, and Manson’s own lush, stacked harmonies. Though the singer mourns a bygone time serving as “the talk of the town” — a cleverly borrowed lament from idol Chrissie Hynde — “Special” secured a place for Garbage in our minds for good. — B. Kress
64. Phil Collins, “You’ll Be in My Heart” (No. 21, Hot 100)
Phil Collins has one of the most impressive chart resumés of the 20th century, with eight Hot 100 No. 1s to his name between Genesis and his solo catalog. So it was no surprise that he hit one out of the park at century’s close with “You’ll Be In My Heart,” the lead single for the Tarzan soundtrack, which he also wrote and composed. Collins gives one of his most memorable performances on the ballad, transforming what could’ve been a cheesy track into a heartfelt lullaby, and thus cementing its status as one of the best Disney songs of all time. The world agreed, as it helped him net his first Oscar trophy for best original song, his second Golden Globe, and even a Super Bowl halftime gig a year later. — XANDER ZELLNER
63. Kelis, “Caught Out There” (No. 54, Hot 100)
In a year stuffed to the gills with breakout solo stars, Kelis’ emergence was relatively subterranean by comparison. But even if the 20-year-old didn’t quite achieve omnipresence right away, she made damn sure the presence she did manage was deeply felt — thanks to debut single “Caught Out There,” a domestic drama made almost painfully visceral by its gut-wrenchingly bilious chorus, and an action-packed Neptunes beat that sounds like a combination of dying fireworks and zooming police sirens. You’d have bet your Y2K bunker on Kelis and Pharrell rivaling Missy and Timbaland for at least the entire decade to come. — A.U.
62. Jamiroquai, “Canned Heat” (No. 1, Dance Club Songs)
Arriving with a jazzed-up intro and a striking bass groove, “Canned Heat” vibrated relentlessly throughout a convoluted period of global political crassness. For Jamiroquai’s front man Jay Kay, taking a back seat to the boogie was the right move; his strategy of riding the beat and dancing until things unraveled resulted in the group’s second No. 1 hit on the Dance Club Songs chart in 1999 — even though it would’ve made just as much sense at the height of disco 20 years earlier. — PAMELA BUSTIOS
61. Fastball, “Out of My Head” (No. 20, Hot 100)
It’s rare to have an iconic organ moment on a ’90s pop song, but Fastball managed to do that within the first few seconds of their own slow-burning top 40 hit. Even more unusual, the song’s skeleton consists largely of its chorus repeated three times — with no verses in between. But it works here, to the point where you might hear the song 100 times before recognizing its bizarre structure, and so much so that in 2017 Machine Gun Kelly and Camila Cabello interpolated “Out of My Head” for their own “Bad Things” collab, a Hot 100 top five hit. — L.H.
60. Vengaboys, “Boom Boom Boom Boom” (No. 84, Hot 100)
Art is just neuroscience, really. Whether it’s a painting or a pop song, different stimuli poke and prod our brains and trigger a reaction, a feeling greater than the sum of its sparks. “Boom, Boom, Boom, Boom!!” — four booms, two exclamation points, it’s all part of the magic — is euphoric, yes, but its synth melodies and chord progression vault it into realm of so-happy-it’s-almost-sad club anthems (see also: No. 7 on our list). And while its lyrics are practically childlike in their talk of a union that lasts “now until forever,” there’s also a fair amount of pent-up frustration, sexual or otherwise, that this marvelous lo-if punk rock cover from 2014 draws out. If you think anybody could throw slap together a cheesy Eurodance beat and some nonsense lyrics and still whip together such a complex cocktail of emotions, just listen to Toy-Box and ask why you’ve probably never heard of them. — N.F.
59. Lauryn Hill, “Everything Is Everything” (No. 35, Hot 100)
Was Lauryn Hill a rapper or a singer? In the late ’90s, it didn’t matter, because Ms. Hill was undeniably gifted in both areas, as proven by her single “Everything Is Everything.” Hill’s worries about injustice and inner-city strife (“Who made these rules? We’re so confused”) on the song’s verses were quickly soothed by her soothing vocals on the chorus (“Change, it comes eventually”). And when Lauryn wasn’t singing, her inner MC floated over the track with elastic ease, proving why she’s “more powerful than two Cleopatras.” — C.L.
58. Sugar Ray, “Every Morning” (No. 3, Hot 100)
Mark McGrath and his Sugar Ray bandmates had an ingenious way of covering up ridiculously raunchy lyrics with undeniable hooks, and “Every Morning” is the prime example. Its uptempo earworm of a riff makes the opening line (“Every morning there’s a halo hanging from the corner of my girlfriend’s four-post bed”) so fun to sing that you don’t even realize what you’re singing about: Pegging, at least according to a Buzzfeed writer’s 2017 revelation (which was maybe confirmed by McGrath himself). Whether listeners realized that or not, they latched on to the song’s playful melody and sent it all the way to No. 3 on the Billboard Hot 100 — and with its bawdy inspiration now revealed, “Every Morning” solidifies Sugar Way as one of the sneakiest pop groups of their time. — T.W.
57. Brad Paisley, “He Didn’t Have to Be” (No. 30, Hot 100)
Brad Paisley’s “He Didn’t Have to Be” isn’t autobiographical, but his earnest, solemn performance certainly sells it that way. Co-written with Kelley Lovelace about Lovelace’s relationship with his stepson, that the song became the first of his whopping 19 country radio No. 1s makes sense; its story of a child’s slowly growing positive relationship with his stepfather is something to which many stepparents aspire. It’s a powerful sentiment that helps the song remain one of Paisley’s most popular to this day, especially if the video’s YouTube comments section is any indication. — K.R.
56. Creed, “Higher” (No. 7, Hot 100)
Creed frontman Scott Stapp belts, “Can you take me higher?” And from the heavens, Mark Tremonti’s guitar answers, bleh-da-BLEH-da-BLEH. The “Higher” chorus is divine intervention from the Christian-inspired blue collar rockers, the lead single from their eventually Diamond-certified sophomore LP Human Clay. The band may have never been cool or edgy, but their slew of hits — “Higher” in particular — are proof of the mountain-moving power you can summon once you toss aside such inhibitions. Whats-his-face from your freshman floor can keep his Creed jokes; he just wishes he could pull off leather pants like Stapp. — C.P.
55. Lil Wayne, “Tha Block Is Hot” (No. 65, Hot 100)
Lil Wayne was all of 16 when his already highly anticipated solo album was released — young enough that he (mostly) honored his mother’s wish not have much cursing on the LP. But the set’s lead single title track, “Tha Block Is Hot,” showed the irrepressible confidence and the irresistible personality that would make Wayne one of the biggest stars of the next century, nimbly tip-toeing over the skittering Mannie Fresh beat as if he actually was scared of getting singed by its heat. And just in case you don’t believe it, he provides his own “tssssss!!‘ sizzle sound effects for evidence. — A.U.
54. Faith Hill, “Breathe” (No. 2, Hot 100)
Faith Hill solidified her crossover appeal with the sultry ballad “Breathe,” released in October of 1999. Effortlessly segueing from a whisper to a belt, Hill’s delicate singing style proved a hit on both pop and country radio: After spending six weeks at No. 1 on Billboard’s Hot Country Songs chart in late 1999 and early 2000, “Breathe” reached No. 2 on the Hot 100. The song’s minimal production and timeless quality has allowed “Breathe” to remain a mainstay on radio playlists and in karaoke joints everywhere. — ANNIE REUTER
53. Q-Tip, “Vivrant Thing” (No. 26, Hot 100)
In 1990, Q-Tip was responsible for one of the great romantic tributes in hip-hop history, with the A Tribe Called Quest classic “Bonita Applebum” — but it took him until the end the decade to release its proper follow-up. Solo hit “Vivrant Thing” shimmied and shook from measure to measure like few other songs of its era, an airtight groove of slapping guitar and hissing hi-hat that kept the funk fresh throughout. But for all the song’s stank, what sets “Vivrant” apart is the genuine reverence on display, Q-Tip raving about his girl’s ability to hold a conversation and go “on and on and on and on and on” behind closed doors with equal ear-to-ear grin. — A.U.
52. Basement Jaxx, “Red Alert” (No. 1, Dance Club Songs)
The hook on this dance floor classic is such a monster, Basement Jaxx knew it wasn’t safe to unleash it on an unsuspecting world at full bore. The impossibly funky bass line first hits us in muffled form before a terrified voice bellows “STOP IIIIIIITTT!!” and they pull the plug. But you can’t contain a runaway riff forever, and after a few false starts, “Red Alert” is careering toward blissful 4/4 oblivion. Fluttering electro echoes, screaming synths and a powerhouse vocal pushed this soulful house classic to the No. 1 spot on the Dance Club Songs chart. — J. Lynch
51. Shania Twain, “That Don’t Impress Me Much” (No. 7, Hot 100)
In 2017, nearly 18 years after the song debuted, Shania Twain revealed exactly why she wasn’t impressed with Brad Pitt that much. (The answer is a sobering reminder of the lack of privacy celebrities face.) But the fact that people still cared about the pop culture references in a two-decade-old song — Hoda Kotb and Kathie Lee Gifford would ask again in November of 2018 — proves its enduring legacy. “That Don’t Impress Me Much” was the third of Shania’s hits to take over Top 40, modeling a sound that would eventually result in Taylor Swift’s pop-country revolution a decade later. — D.W.
50. Blink-182, “What’s My Age Again?” (No. 58, Hot 100)
It’s hard to hear “What’s My Age Again?” without imagining the Blink-182 boys running naked through the streets with nothing but tattoos and pixels keeping them modest. That iconic music video was a perfect match for the anthem of immaturity, which basically served as the pop-punk trio’s career mission statement. Why act your age if it means giving up prank phone calls and cartoons? Boring! — K.A.
49. Fiona Apple, “Fast As You Can” (No. 20, Alternative Songs)
Fiona Apple stood as far away as possible from the manufactured pop machine of the ’90s — an isolation which resulted in her emergence as a singular talent of her generation. Any trace of youthful susceptibility, however, was shattered on the scurrying “Fast As You Can,” one of Apple’s most mature hits. The lyrics hint at the highs and lows of a relationship, while her moody vocals (“I’ll soar the uneven wind, complain and blame the sterile land”) ricochet through the spellbinding pulsations of the song’s drums and percussion. — P.B.
48. Aphex Twin, “Windowlicker” (Did not chart)
Forget The Lonely Island — Aphex Twin nailed the hip-hop music video parody way before “Turtleneck and Chain.” That bikini-clad, champagne-soaked women would be slow-mo shaking it to a dance song as fundamentally weird as “Windowlicker” is almost as unthinkable now as it was then. Opening with Richard D. James’ vocal-modulated breathy growls and pixilated shards of digital melody, “Windowlicker” exists out of time, in some black hole where noise, ambient, breakbeats and turntable technics have collapsed into some version of pop we can barely comprehend. — H.B.
47. Backstreet Boys, “Larger Than Life” (No. 25, Hot 100)
Everything about the title of “Larger Than Life” felt fitting in 1999: the music video (and its price tag), its live performances, AJ McLean’s maniacal scream to kick off the song, a bona fide guitar solo in a Backstreet Boys song, that hook. This was an event, Millennium’s way of ringing in the era for which it was named, “Drag Me Down” for an earlier generation. But even minus context, “Larger Than Life” remains unimpeachably titanic, and no BSB chorus has been able to live up to it since. — K.R.
46. OutKast, “Da Art of Storytellin’ (Pt. 1)” (No. 67, R&B/Hip-Hop Songs)
OutKast’s Big Boi and André 3000 knew they had the lyrical hot hands when they positioned hip-hop as a platform to “shoot game in the form of story raps” on “Da Art of Storytellin’ (Pt. 1).” The duo trade tales with dexterous precision over a hustling beat that leaves little breath to look back and reflect. Its multi-generational impact still endures, from the Watch the Throne hook spun from a chilling 3 Stacks line to J Cole’s direct homage on “Land Of The Snakes.” — B. Kress
45. Hole, “Malibu” (No. 81, Hot 100)
“Malibu” offered a stark contrast to “Celebrity Skin,” the cheeky, snarling title track off Hole’s 1998 LP. Instead of Courtney Love’s scathing wit and blistering power chords, “Malibu” — which she co-wrote with Hole guitarist Eric Erlandson and Billy Corgan — peeled back the tough exterior of her songwriting to reveal a cathartic, grieving softness. Celebrity Skin went on to score the band’s only three Grammy nominations, and one of those was for “Malibu,” in the best rock performance by a duo or group category. — H.H.
44. Brian McKnight, “Back at One” (No. 2, Hot 100)
Brian McKnight’s velvety vocals and memorable falsetto shine on “Back at One.” A heartfelt song the R&B stalwart penned solo, “Back at One” has McKnight promising to fiercely love his lady while making women everywhere swoon. One of his biggest hits, “Back at One” was covered by countless acts, including country singer Mark Wills as well as Brazilian artist Ivete Sangalo, who recorded a Portuguese version. A No. 2-peaking smash on the Hot 100 chart, “Back at One” remained a top contender as the wedding song of 1999. — A.R.
43. LFO, “Summer Girls” (No. 3, Hot 100)
What do Paul Revere, New Kids on the Block and Abercrombie & Fitch have in common? They all make a cameo in LFO’s oddball “Summer Girls,” perhaps the most unconventional love song of the late ‘90s. A majority of the lyrics are as random as that combo — yet, the song manages to tell the tale (and convey the feeling) of a summer romance that fizzled out. Frontman Rich Cronin’s rap-like delivery of lines that connect the lovelorn story with pop culture references (“Call you up but what’s the use?/ I like Kevin Bacon/ But I hate Footloose”) is so smooth, the song is way more lovable than it would be if the verses made sense. Tied together by an unmistakeable guitar riff and a gleefully unnecessary record-scratching sound effect, “Summer Girls” is proof that sometimes the most outlandish tunes are the ones that become timeless. — T.W.
42. Mos Def, “Ms. Fat Booty” (No. 54, R&B/HIp-Hop Songs)
Led by a hypnotic sample of Aretha Franklin rarity “One Step Ahead,” Mos Def glides through “Ms. Fat Booty,” his debut single as a solo artist. But while Franklin’s voice ties the song to a classic sound, Mos Def’s story feels timeless, perhaps even timely in 2019: He presents the titular bombshell as a thirst trap, years before Instagram turned us all into prospective thirst traps. The song’s final lines however, reveal a twist that positions his narrator as a hopeless romantic, no match for Ms. Fat Booty’s pansexual, sex-positive free spirit. — E.F.
41. Lit, “My Own Worst Enemy” (No. 51, Hot 100)
From its opening guitar roar, “My Own Worst Enemy” lets you know you’re about to listen to an absolute jam. The pop-punk sound exemplified by the song, created by repetitive guitar riffs, sing-song melodies and lyrics about regrettably immature activity — like intoxicatedly parking your car in the front yard and having to break into your own house — took off in 1999, and later helped usher in the success of bands like Sum 41 and New Found Glory in the early 2000s. But above anything else, what truly makes the song hold up to this day is how universal the message is: Everybody makes (drunk) mistakes. — B. Kaminsky
40. Lou Bega, “Mambo No. 5” (No. 3, Hot 100)
In the United States, “Mambo No. 5” arrived at the perfect time: the economy was booming, summer was just getting started, and this song’s horns were too invigorating not to dance along. The fact that it was a German artist reworking a Cuban song for a smash hit that really took off in Australia helped underline its global appeal — not to mention the fact that the Radio Disney edit, where the lineup of Bega’s female interests was replaced by Disney characters, made it ubiquitous among kids, too. The song had something for everybody: except for source artist Perez Prado’s estate, who sued Bega over the sample. — D.R.
39. Britney Spears, “(You Drive Me) Crazy” (The Stop Remix) (No. 10, Hot 100)
The third single from Spears’ debut album amped up the drama of “…Baby One More Time,“ but it was the remix included on the soundtrack to the Melissa Joan Heart-Adrian Grenier rom-com Drive Me Crazy in 1999 that really took her “oh baby baby” yearning and twisted it into pounding obsession. The reworked version was hardly unrecognizable — you still have that ratting cowbell, the perfect sound to evoke a screw coming loose your brain amid an all-consuming crush — but Spears’ re-recorded vocals, a new spine-tingling intro and her titular ”Stop!“ interjection in the reimagined bridge made it something truly worth losing your mind over. — N.F.
38. Dixie Chicks, “Cowboy Take Me Away” (No. 27, Hot 100)
If Shania and Faith were crossing over with their pop-ified twangs, the Dixie Chicks were holding down the country fort on their home turf, with their signature powerful harmonies and yearning fiddle. “Cowboy Take Me Away” expresses the beautiful melancholy of a different time, and a dream that the love of a good man might save you. It would be four years until lead singer Natalie Maines’ criticism of George W. Bush and the war in Iraq almost unfairly destroyed the Chicks’ career. Listening to “Cowboy” now reminds us of the power of their voices. — D.W.
37. Lee Jung Hyun, “Wa” (Did not chart)
Before K-pop concepts settled into a semi-standardized taxonomy, there was Lee Jung Hyun. Known as the Queen of Transformation, her shapeshifting performances feel like self-contained worlds of character acting. This theatricality bolsters the blend of the historic and the space-age on debut single “Wa.” Traditional instruments give way to pulsating beats, as the song confronted Korea with the genre that would define her career: techno. Her futuristic vision paid off, with “Wa” now being heralded as a classic of first-generation K-pop. No wonder Lady Gaga personally asked Lee to open her concert in 2009. — CAITLIN KELLEY
36. KoRn, “Freak on a Leash” (No. 6, Alternative Songs)
Korn’s signature single is forever linked to its cinematic music video, which blended grim comic-book animation with live action, and dominated MTV’s Total Request Live. Yet the song is also the purest distillation of Korn’s appeal at their turn-of-the-century commercial height: full choruses, twitchy guitar effects, Jonathan Davis’ purposely creepy vocal approaches, nonsensical bridges. Those seeking to defend the days of nu-metal need only point to the rush that “Freak on a Leash” still provides upon repeat listens. — J. Lipshutz
35. Mandy Moore, “Candy” (No. 41, Hot 100)
If Britney Spears and Christina Aguilera were the cool older sisters throwing the party in 1999, Mandy Moore was more like the younger one most likely to narc them out. Moore’s debut single, “Candy,” dropped that August when she was just 15 years old, and compared to her predecessors, her sugary-pop sound and squeaky-clean image veered more tween than teen. It may have only peaked at No. 41 on the Hot 100, but between the shimmering, bell-like effect at the song’s start and the “missing you like candy” lyric — not to mention the spoken-word bridge, with the too-perfect rhyming of “Candy” with “Mandy” — the sweetness of “Candy” was addictive and unmissable. The more guttural “aw, babaaay”’s that dotted the song kept it from coming off cutesy, while in the video, midriffs were bared, though none of them belonged to Moore. — C.W.
34. Enrique Iglesias, “Bailamos” (No. 1, Hot 100)
The rise to omnipresnce of Enrique Iglesias’ “Bailamos” proves that back in 1999, pop music was dominating the Latin industry, and vice-versa. The flamenco-inflected mid-tempo anthem is an invitation to dance in a romantic date — one that quickly proved irresistible for all audiences, as the song peaked at No. 1 on Billboard Hot 100 and spent two weeks on top of the chart. Released on both the Wild Wild West soundtrack and Iglesias’ debut English-Language album Enrique, “Bailamos” marked the first crossover smash from an artist who’d stay a regular presence on pop and Latin radio well into the 21st century. — SUZETTE FERNANDEZ
33. Tal Bachman, “She’s So High” (No. 14, Hot 100)
Let’s be honest: Few romantic odes are as pure as Tal Bachman’s buoyant pop-rock paean to a woman so far out of his league, he won’t even bother to entertain the idea that “anything should happen.” From its references to Cleopatra, Joan of Arc and Aphrodite to its oh-so-’90s music video (check out Tal’s curly blonde locks!) and the euphoric, sing-your-heart-out “hiiiiiiigh” of the chorus, the song is so wholesome it hurts — and probably screwed up every ‘90s kid’s expectations of love and relationships for good. “She’s So High” may have been a one-hit-wonder for Tal, son of Canadian rocker Randy Bachman, but his earnest depiction of falling hopelessly in love will be stuck in our heads forever. — TATIANA CIRISANO
32. The Roots feat. Erykah Badu, “You Got Me” (No. 39, Hot 100)
Despite being one of the most recognizable outfits in all of hip-hop for over 20 years now, The Roots have still visited the Hot 100’s top 40 only once, with 1999’s Erykah Badu collab “You Got Me.” The dual-perspectived relationship story ensured the group’s cult following would have some at least overlap with pop audiences, and also gave the era one of its best love songs — an ode to commitment and consistency and simply being there through tough times. The song’s minor-key melody provides the undercurrent of doubt forever plaguing its two narrators, as does its unexpected drum-and-bass outro and Badu’s “psyyyche” fake-out about flirting with a ballplayer. But it always circles back to that chorus, providing the soft-spoken assurance we all hope to get at the end of the day: “Baby, don’t worry, you know that you got me.” — A.U.
31. Madonna, “Beautiful Stranger” (No. 19, Hot 100)
The psychedelic accents on this soundtrack one-off was mostly a new sound for Madonna, taking older fans all the way back to such ’60s classics as Love’s “She Comes in Colors.” Younger fans just thought it was a cool, intriguing record, integrating the flower power-era sensibilities from the Austin Powers sequel it accompanied, with a modern pop sensibility that allowed it to fit in alongside Britney and Christina on ’99 top 40 radio. Madonna co-wrote the song with William Orbit — with whom she had collaborated on her Ray of Light album — and it won a Grammy for best song written for visual media, still the only Grammy that Madonna has won to date for her songwriting. — P.G.
30. Eiffel 65, “Blue (Da Ba Dee)” (No. 6, Hot 100)
Easily the best song about a color from an Italian group with a French name, Eiffel 65’s “Blue” is the Fred Schneider techno jam we never knew we needed. It was dismissed as ridiculous Eurocheese by detractors when it started making headway in the States, but that’s exactly why this works: With high camp vocal delivery, Auto-Tune trills and baby-talk non-lyrics (which many misheard as “without a beat I would die”), “Blue” is the absurd European dance-pop song to end all absurd European dance-pop songs. — J. Lynch
29. Björk, “All Is Full of Love” (Did not chart)
Twenty years before androids had facial expressions, robo-Björk made out with another automaton in the sweet, unsettling music video for “All Is Full of Love.” Director Chris Cunningham’s late-‘90s computer animation was so advanced that android Björk could have been an extra in recent robots-are-coming-to-kill-us films like Ex Machina. Sonically, a trip-hop beat clanks hypnotically in the background like machine gears, while spine-tingling harps and violins carry the song’s gently uplifting message of affection for all. — H.B.
28. Ol’ Dirty Bastard feat. Kelis, “Got Your Money” (No. 33, Hot 100)
Music may never see another artist as idiosyncratic as Ol’ Dirty Bastard, a rapper as crude and wild as he was unapologetically himself — and this song, more than almost any other in his catalog, embodies his eccentricities to the max. Whether it’s the too-literal-for-its-own-good opening verse, or the drawn-out warble at the end of the second chorus, or just his generally deranged and unpredictable flow, ODB was a one-of-one in every single way, managing to bring Kelis’ earworm hook into his surreal world of excess and insanity — and score his biggest crossover hit in the process. — D.R.
27. Sixpence None the Richer, “Kiss Me” (No. 2, Hot 100)
“Kiss Me” is mushy and cute and sweet and vulnerable — it sounds like falling for someone, which is why it connected with Dawson’s Creek viewers, just about every teen movie within two years of the millennium, and countless proposals in the years since. Sixpence None the Richer’s breakthrough hit spent 16 weeks in the Hot 100’s top 10, peaking at No. 2 in May of ’99 — the Nashville folk-pop outfit’s only non-cover song to reach a Top 40 audience. But it’s lived on in the language of falling in love (and wedding cover bands) so well, it still feels like it’s riding off into the sunset. — C.P.
26. Mariah Carey feat. Jay-Z, “Heartbreaker” (No. 1, Hot 100)
Few artists did more to bridge the gap between pop and hip-hop in the ‘90s than Mariah Carey, who made featured guest appearances by rappers a regular part of the diva playbook. She’d been doing it for years by the time she teamed up with Jay-Z for the lead single off Rainbow, but “Heartbreaker” — built around a sample of Stacy Lattisaw’s 1982 novelty hit “Attack of the Name Game” — perfected the formula with her swooning vocals and his playful rhymes. In perhaps one of pop culture’s luckiest close calls, Carey reportedly planned to put “Heartbreaker” on her ill-fated Glitter soundtrack, until the project got delayed. But the song ended up getting its own mini-movie treatment anyway: The “Heartbreaker” music video, one of the most expensive videos ever made at the time, finds Carey coming to blows with devious romantic rival named Bianca (also played by Carey), in a fight scene so iconic Carey has been recreating it on her current world tour. — N.F.
25. Celine Dion, “That’s the Way It Is” (No. 6, Hot 100)
As a singles artist, Celine Dion’s stardom in the U.S. almost exclusively resided in the 1990s; the Canadian superstar has collected 10 top 10 hits on the Hot 100 chart, beginning in 1990 with “Where Does My Heart Beat Now” and ending at the turn of the century with “That’s the Way It Is.” When the latter was released in ’99 as a new single on a greatest hits compilation, it swerved away from the high drama of Dion’s world-conquering then-recent hit “My Heart Will Go On,” and toward something much more pillowy, more in the vein of light adult-contemporary fare by country-pop artists like Faith Hill and Shania Twain. The slight turn was masterful: “That’s the Way It Is” embraces the intrinsic corniness of its self-affirming message, as Dion delivers plenty of winks in between a typically stellar vocal performance. She’d never impact pop radio quite the same way after this, but what a blissful way to go out. — J. Lipshutz
24. Red Hot Chili Peppers, “Scar Tissue” (No. 9, Hot 100)
Having weathered two motorcycle accidents and the thorny departure of mid-’90s guitarist Dave Navarro, the Red Hot Chili Peppers were desperately in need of a rebound by ‘99. The wistful, confessed “Scar Tissue” was the perfect comeback, mixing drawled lyrics about loneliness with subtle motivation (“I’ll make it to the moon if I have to crawl”) and one hell of a guitar solo from returning axeman John Frusciante. In his autobiography (also titled Scar Tissue), bandleader Anthony Kiedis looked back on the song as a “phoenix-rising-from-the-ashes vibe,” and he was right — “Scar Tissue” won a Grammy and served as the lead single off Californication, the similarly Grammy-winning LP that would re-establish RHCP as superstars. — T.C.
23. Jay-Z feat. Amil, “N—a What, N—a Who (Originator 99)” (No. 84, Hot 100)
The beginning of Jay-Z and Timbaland’s two decade-long musical relationship kicked off with the former’s Vol. 2… Hard Knock Life set, where the latter lent his production to two songs — one of which found the pair jetting into outer space. “N—a What, N—a Who (Originator 99)” saw Jigga making a rare return to the rapid-fire, double-time flow that he abandoned once his stardom went interstellar. But when Timbaland creates a melody that sounds like a rush to beat the clock before the ball dropped on 2000, he had no choice but to mimic that head-spinning feeling, with the same intensity that he and featured rapper Jaz-O had on their funky 1990 collaboration, “The Originators.” — B.G.
22. Whitney Houston, “It’s Not Right, But It’s OK” (No. 4, Hot 100)
Word to the wise — don’t ever turn against Whitney Houston. For nearly two decades, some critics derided her as an “Ice Queen,” all voice and no personality. On “It’s Not Right,” Newark’s Nippy takes a flamethrower to that real-life criticism, just as she scolds her cheating partner in the lyrics. Old Whitney might sob in a syrupy ballad, but in ’99 she professed, “There’s no more tears left here for you to see,” backed by a slick Darkchild beat. Throw in her revamped look in the music video — straight hair that covers one eye, a thick black choker and a strapless leather gown — and the only disappointment is wondering how Houston’s career would have went had her full personality been on display like this from day one. — T.A.
21. Smash Mouth, “All Star” (No. 4, Hot 100)
“All Star,” the second single from Smash Mouth’s 1999 album Astro Lounge, hit the ground running, peaking at No. 4 on the Hot 100 that August and spending 30 weeks on the chart. After all, its verses were immediately catchy — especially since the song launches right into them — and the off-kilter lyrics were tons of fun to sing along to. It then largely dropped off the charts until 2017, but “All Star” must only be discussed in tandem with its meme-ability, which arguably began the moment it featured in 2001’s Shrek. By 2017, hundreds of remix videos — mildly viral clips that make the rounds among meme lovers, but typically cap out at under one million views — had driven it back into pop culture and onto the charts, spending a total of 72 weeks on the Rock Streaming Songs chart thus far, and even peaking at No. 4 in 2019. All that glitters is gold! — GAB GINSBERG
20. DMX, “Ruff Ryders Anthem” (No. 94, Hot 100)
Whenever DMX’s “Ruff Ryders Anthem” came booming through the speakers, you already knew the drill: “Stop, drop,” and the rest was self-explanatory. X’s rowdy persona coupled with his genius for hood bangers made him a game-changing force in the late ’90s: Ask any DJ, and they’ll tell you why this record (which was released in ’98 but took till ’99 to hit the Hot 100) rang off at any concert and/or sporting event. Whether you’re popping a wheelie with your crew, or just ready to mob with your homeboys, make sure to cue up “Ruff Ryders Anthem” in hopes of elevating your team’s morale. — C.L.
19. Len, “Steal My Sunshine” (No. 9, Hot 100)
Ontario siblings Marc and Sharon Costanzo didn’t see their sole Hot 100 hit peak at No. 9 until September, but “Steal My Sunshine” was arguably the song of the summer of 1999, both on the radio and on MTV. At a time when the Y2K scare and other millennial fear-mongering was responsible for an annoying case of cultural psoriasis, the track was a breezy balm, driven by a giddy sample from the bridge of the Andrea True Connection’s disco classic “More, More, More.” The repeated piano-and-wood-block earworm, paired with the interplay of Marc’s rasp and Sharon’s sweet ethereal sing-speak, still sounds, all these years later, like a day at the beach. As for the lyrics? Marc reportedly wrote them after attending a rave, and they sound like it: “My mind was thugged, all laced and bugged, all twisted, wrong and beat/ A comfortable three feet deep.” Whatever you say, bro. — F.D.
18. Fatboy Slim, “Praise You” (No. 36, Hot 100)
The Torrance Community Dance Group may not have ever quite reached the technical heights of Martha Graham or Alvin Ailey — but in 1999, co-directors Roman Coppola and Spike Jonze led the rag-tag, amateur (not to mention, fictional) assembly of actor/dancers to an inspired performance outside a Los Angeles multiplex that ultimately won three MTV Video Music Awards. Set to Fatboy Slim’s sample-heavy, Grammy-nominated pop classic, “Praise You,” Jonze and co. jump, fly, shimmy, breakdance, and much more. The group’s goofy charm and stone-faced sincerity matches the song’s communal, piano-led (and soul-sampled) jubilance, combining for an iconic four minutes of late-90’s dance-pop. — E.F.
17. Missy Elliott feat. Nas, Eve & Q-Tip “Hot Boyz” (No. 5, Hot 100)
Time and time again, Missy Elliott brings out the best in her collaborators. Whether it was her partnership with Aaliyah and Timbaland, her recent release with Lizzo, or the rowdy posse remix to “Hot Boyz,” Missy unlocks potential. The third single from her sophomore album Da Real World set a Hot Rap Singles record, topping the chart for 18 weeks straight. Nas arrived in full Escobar regalia, Eve provided the vivid image of “thugs open wide,” fucking with their tongues out, and Q-Tip went with tried-and-true dick-as-gun wordplay. Combined with Timbo’s cinematic future-bright production and Missy’s sultry hook, it all sounded, well, hot. — R.S.
16. Foo Fighters, “Learn to Fly” (No. 19, Hot 100)
Forget the music video, even if it remains one of the Foo Fighters’ best in a lineup of goofy, often over-the-top visuals. On its own, “Learn to Fly” is a triumph from the opening riff (and listen to said riff; it’s almost as though the band knew that). That was probably on purpose, because following up songs as action-packed as “Everlong” and “My Hero” was going to be no easy task. It’s sunny, catchy, poppy — and that’s just the chorus, to say nothing of its bridge, which if surgically implanted into another Foos song as the main melody would probably make that new tune a gem in its own right. And you know what, on second thought, don’t forget the music video: The moment Grohl’s pilot looks out the airplane window and hallucinates Grohl’s flight attendant flying beside them is comedy gold. — K.R.
15. Destiny’s Child, “Bills, Bills, Bills” (No. 1, Hot 100)
Kevin “She’kspere” Briggs and Xscape’s Kandi Burruss specialized in telling off deadbeat men through playful R&B songs in 1999, first in February with a song still to come on this list, and then in June with Destiny’s Child’s “Bills, Bills, Bills,” which hit No. 1 on the Hot 100 by July. “Bills” was the sassy, harpsichord-synth-led first single from the group’s second album, The Writing’s on the Wall, and also featured the penwork of the quartet, whose membership was soon to be reshuffled. Pre-Beyoncé-only Knowles shines in the track’s lead role, scowling in the hair-salon-set music video and turning “cell phone” into a six-syllable phrase whose bill you definitely could not afford. Freeloaders, begone! — C.W.
14. Dr. Dre feat. Snoop Dogg, “Still D.R.E.” (No. 93, Hot 100)
With the now-iconic staccato piano hook to “Still D.R.E.,” all-time West Coast legend Dr. Dre reemerged from behind the boards and ushered in his next episode, the 2001 era. On an all-encompassing career comeback track co-penned by Jay-Z at his braggadocious peak, and featuring trusted collaborator Snoop Dogg in the passenger seat, Dre weaves his accomplishments like his debut classic The Chronic and his signing of the unlikely rap phenom Eminem into an indisputable flex that still rings true today. Though his voice may not dominate the conversation constantly, his enduring influence on hip-hop will always speak for itself. — B. Kress
13. Ricky Martin, “Livin’ La Vida Loca” (No. 1, Hot 100)
A pop song so perfect that it can survive “Her skin’s the color mocha” serving as a crucial lyric, “Livin’ La Vida Loca” became one of pop radio’s most inescapable songs in 1999, while also turning Ricky Martin into a platinum superstar and sparking a new Latin-pop explosion. The tsunami that this song caused was deserved: the combination of canned horns, surf-rock guitar and lyrics about an irresistible, particularly sinister woman (“She took my heart, and she took my money/ She must’ve slipped me a sleeping pill” is dark, honestly) is led by the devastating charm of Martin. The former Menudo member sounds like he’s having a blast telling this bad-love story, based on his rampant exclamations of “come on!” and “woooo!” Martin scored a couple more pop hits in the U.S. in the following years, and has become an important figure in both the Latin music and LGBTQ communities, but he’ll likely be best remembered for this supernova of a single, which still sounds fresh today. — J. Lipshutz
12. Shania Twain, “Man! I Feel Like a Woman” (No. 23, Hot 100)
Let’s go, girls. Col. Twain is on the warpath in the most explosive of her zillion Come On Over hits, and that six-note synth riff is her own personal “Ride of the Valkyries.” But it’s not freedom, independence or even auto-mo-bills she’s fighting for, just a woman’s prerogative to have a little fun. On those grounds — and really by just about every other standard imaginable — “Man! I Feel Like a Woman” is Mission: Accomplished, a four-minute romp of raised voices, short skirts and hair hanging all the way down, which sounds like it’s setting a new high score every time that synth hook goes off. When Shania sings about the best part about being a woman, you take her at her word, because she sounds so obviously like she’s living it. — A.U.
11. Christina Aguilera, “Genie in a Bottle” (No. 1, Hot 100)
“Genie in a Bottle” not only launched Christina Aguilera’s career as the lead single off her self-titled debut, but also set her apart from her teen-pop contemporaries with its more soulful sound (thanks to Aguilera’s roaring vocals, even in her teenage years), its squelching beat, and self-respecting lyrics that set a precedent for how to handle early-on sexual encounters. (1. Don’t give it away to just anyone blowing kisses your way. 2. Any potential suitor needs to make a big impression.) In 1999, Aguilera performed the growing hit on Beverly Hills 90210; in 2014, it soundtracked tennis player Eugenie Bouchard’s US Open games. Today, the song remains one of the enduring pop star’s most iconic, appearing as the second song off the set list on her recent Liberation tour. — L.H.
10. Eminem, “My Name Is” (No. 36, Hot 100)
While the West Coast was Crip-walking over gangsta beats and the East Coast was boasting about its endless supply of cash and hoes, a young white kid from Detroit infiltrated. “My Name Is,” Eminem’s first single from his The Slim Shady LP major-label debut, was a blunt introduction to his witty (and temperamental) sense of humor. “Hi, kids! Do you like violence?/ Wanna see me stick nine-inch nails through each one of my eyelids?” he sarcastically asked in the tone of a college professor. Over Dr. Dre’s brilliantly cartoonish sample of Labi Siffre’s 1975 single “I Got The,” Slim Shady previews every element that he’s now become infamous for: He shits on his mother, makes gross misogynistic jokes about female celebrities, foreshadows “Stan” with drunk-driving threats and just generally mocks contemporary pop culture. “My Name Is” quickly became a top 40 smash, was certified 2x Platinum and earned Eminem his first Grammy for best rap solo performance — an early sign that sticking to his unapologetically flippant formula would be the way to go. — B.G.
9. Jennifer Lopez, “Waiting For Tonight” (No. 8, Hot 100)
Jennifer Lopez’s 1999 debut album On the 6 delivered many bangers, from the roof-raising “Let’s Get Loud” to the alluring “If You Had My Love.” But it’s “Waiting for Tonight” that stands out among her hits all these years later. The themes are universal, the music is infectious, and the chorus remains timeless. “Tonight” oozes sex appeal, and not just because of Lopez’s sultry vocals — or the skimpy outfits she wears in the video (set, oddly, in a jungle-cum-dance-club). The strums of the guitar and the pulsating beat perfectly complement the lyrics of someone longing for their lover. And her breathless “ohhhhhh-ohhhh-ohhhs” give off a satisfied, post-coital feeling. If “Tonight” premiered today, it would still be a smash — and we can only imagine what Alex Rodriguez’s reaction would be. — D.W.
8. Blink-182, “All the Small Things” (No. 6, Hot 100)
All that lovey-dovey “your ride, best trip” stuff? Blink-182 really meant it: Tom DeLonge wrote “All the Small Things” about his then-girlfriend (now wife), and Mark Hoppus met his future wife on the set of its iconic music video. So while Blink spent its most glistening pop moment clowning on the Backstreet Boys, much of what makes “All the Small Things” so great was is its willingness to cast Mark, Tom, and Travis as a snickering, skate park boy band. They’re a little more self-aware, but they also know a lot of their fans really want to see them in their underwear and that na-na, na-na’s are just as infectious as bye bye bye‘s. Producer Jerry Finn plays pop-punk Max Martin, spit-shining Tom DeLonge’s power chords like supersonic laser blasts, making Travis Barker’s popcorn drums blast off like rockets. These days, both Blink and BSB are still scoring hits alongside Vegas residences, and we only hope it’s not too awkward when they run into each other at Cirque du Soleil. — C.P.
7. Cher, “Believe” (No. 1, Hot 100)
The song that helped Cher set a record for the longest gap between Hot 100 toppers is most famous, of course, for its vocal effects: an extreme application of a then-little known tool called Auto-Tune that most people mistook for vocoder at the time. But aside from what we can assume is some light pitch correction, the song’s money note — the way Cher sings the second syllable of the word “believe,” in a way only Cher can — doesn’t need any technological help to pierce your brain’s pleasure center. The song’s legacy is so much more than her vocal performance, anyway: While Cher isn’t officially credited as a songwriter here, she’s said in interviews that she altered the second verse to make it less “whiny” and more empowering, turning what would have been just a song about throwing your hands up and licking your wounds into “I Will Survive: Ibiza.” And it doesn’t hurt that a song about finding a new lease on life after you’ve been written off coincided with a musical reinvention that spawned one of the best-selling singles of all time, let alone of her career — a rare eclipse of the meta and the material that’s still resonating across dance floors decades later. — N.F.
6. Lauryn Hill, “Ex-Factor” (No. 21, Hot 100)
“Ex-Factor” is a single of such profound compositional brilliance and singular performance that discussing it in its entirety is far too daunting for a best-of blurb. So let’s simplify things by focusing only its opening line: “It could all be so simple/ But you’d rather make it hard.” Even if the rest of the song was instrumental, you’d understand it perfectly from those 12 words, which express absolutely everything: the pain, the confusion, the willful naivete, the sheer misery of bliss being at your fingertips and still 10,000 miles away. It also sets up the song both in tone — Hill’s voice goes from ecstatic to yearning to strained and back through the four measures — and in form, as Ms. Lauryn serves as her own subconscious underneath her main vocal, ad libbing in the in-between spaces and harmonizing with herself for emotional backup. And oh yeah: It also calls back to the song’s sample source, the Wu-Tang Clan’s “Can It Be All So Simple,” whose lurching bass and see-sawing drums give the song its backbone, allowing it to muscle through the hurt. This is why even a song as great as Drake’s “Nice For What” borrowing elements from “Ex-Factor” feels inherently sacrilegious; when a song has this much soul bursting through its seams, trying to get away with stealing just a piece of it is never that simple. — A.U.
5. Santana feat. Rob Thomas, “Smooth” (No. 1, Hot 100)
A viral tweet from last year posed a question about which phrases you could say that would immediately bring a song to mind — think “It’s been…” for Barenaked Ladies’ “One Week,” or “SomeBODY,” said in exactly the right way, for Smash Mouth’s “All Star.” When it comes to this then-ubiquitous Santana song, you could substitute any number of things: the opening drum fill, Santana’s first livewire guitar lick, or just about every single lyric that Rob Thomas growls across its four-plus minutes, highlighted by the classic opener, “Man, it’s a hot one” (something of a meme in and of itself).
But that serves to illustrate just how deeply embedded into the public consciousness this song became, even 20 years after its initial release, sparking strong emotions positive or negative among anyone who hears it. Sorta cruel that one of the hands-down greatest guitarists to ever pick up the instrument is largely remembered by an entire generation as “the guy who plays guitar on that Rob Thomas song,” but Santana probably doesn’t care: It’s rare enough to deeply influence pop culture once, much less multiple times, 30 years apart. He’ll be fine. — D.R.
4. Juvenile feat. Mannie Fresh & Lil Wayne, “Back That Azz Up” (No. 19, Hot 100)
Among songs that create social experiences — soundtrack a party, pack a dance floor — “Back That Azz Up” is especially powerful. The 15 second string intro acts like an alarm clock, letting you know what time it is. As Mannie Fresh put it, “When that comes on, people wake up.” Fresh began his musical career as a club DJ and he didn’t lose that perspective as a producer. Juvenile’s lyrics are equally to the point, favoring simplicity and an oft-imitated flow: “Girl you’re working with some ass, yeah/ You’re bad, yeah.” (Don’t mistake simplicity for blandness, though — “hoes frown when you pass” is one of the most indelible images in hip-hop.)
Released in late 1998 on 400 Degreez, the song didn’t become a chart-climbing single until 1999, much to the surprise of Juvenile. “I didn’t think people in New York and L.A. — people that weren’t from my area or are used to [bounce music] — would like it,” he told Complex in 2012. But as the 20th century closed, Juvenile broke down regional walls in hip-hop, both with “Back That Azz Up” and with Jay-Z’s appearance on the “Ha” remix. You can draw a straight line from Juvie’s success to the post-regional styles of A$AP Rocky and Drake, to the Nola sound of Drizzy’s recent No. 1 smash “In My Feelings.” But 20 years later, there’s no replacing “Back That Azz Up.” Cash Money Records still taking over for the ’19 and beyond. — R.S.
3. Backstreet Boys, “I Want It That Way” (No. 6, Hot 100)
By April of 1999, Max Martin had already helped the Backstreet Boys notch three top 5 hits on the Billboard Hot 100, including a No. 2 peak with “Quit Playing Games (With My Heart).” While no BSB song reached a higher feat after that, “I Want It That Way” — whose Hot 100 peak was hurt by its single not being widely available for sale at its commercial peak — didn’t need chart validation to become the biggest hit of their career. The second the plucking guitar begins, ’90s babies are transported back to their poster-plastered bedrooms and Walkman jam sessions, thrusting their fists in the air to sing “You are my fire/ The one desire.”
But the song’s staying power certainly doesn’t rely on nostalgia: The mid-tempo ballad’s bombastic production and epic key changes are striking whether you’re hearing it for the first or four-thousandth time, and the song even earned a record of the year Grammy nomination in 2000. And though its lyrics are rather baffling — Chrissy Teigen’s attempt to set the record straight led to the Backstreet Boys admitting that the “it” is still inexplicable — “I Want It That Way” isn’t just a definitive boy band classic: it’s an all-time pop staple. — T.W.
2. TLC, “No Scrubs” (No. 1, Hot 100)
Obviously, the ladies of TLC — T-Boz, Left Eye and Chilli — didn’t need a man to take care of them, but they weren’t trying to date a freeloader either. Enter their 1999 song (and public service announcement) “No Scrubs.” What is a scrub, you might ask? Don’t worry, the lead FanMail single’s lyrics spell it out: a guy who has no car, lives with his mom and/or doesn’t take care of his kids is not going to earn the trio’s love. “I definitely don’t think it’s the first song where females talk about a dude, but we really went in,” Rozonda “Chilli” Thomas told Billboard in 2014 of the song, written by Xscape’s Kandi Burruss and Tameka “Tiny” Cottle and produced by Kevin “She’kespere” Briggs.
Beyond the scathing message to dudes catcalling from the passenger seat, Briggs’ production brilliantly combined an acoustic guitar riff with a hip-hop beat to create a timeless sound that would fit in nicely on modern-day radio. And speaking of radio, one of the most underappreciated parts of the song is the late Lisa “Left Eye” Lopes’ inimitable rap verse, which was edited out for most airplay and isn’t on the album version. Thankfully, the Hot 100 No. 1’s space-age music video gave the verse the shine it deserved, particularly the crafty “spectacular/vernacular/back to ya” combination — and the only time FILAs was ever rhymed with señoritas. — K.A.
1. Britney Spears, “…Baby One More Time” (No. 1, Hot 100)
Not just a career-making song, the Max Martin-helmed debut single from Britney Spears was a watershed in pop music; like similar game changers from MJ or The Beatles, there is pop prior to “…Baby One More Time,” and there is pop thereafter. Minimalist in composition yet maximalist in delivery, instantly memorable yet endlessly listenable, “Baby” is a shotgun wedding between lithe funk-pop and the Swedish music machine. It’s everything that absolutely should not work, yet it somehow tracks as dangerous, bold and visionary.
“Baby” was also born at the right time. Aside from Mariah, the pop titans of the ’80s were never really matched during the ’90s, a decade defined by alt-rock and hip-hop’s ascendance. The American market was long overdue for new blood to arrive and assume the crown — or at least throw down the gauntlet in an MTV-documented bloodbath for TRL supremacy. And with her calculated mixture of teenage naïvete and Lolita coquettishness oozing through the mic (not to mention the visual, whose concept Spears fought her director over, insisting it take place in high school vs. outer space), Britney knew exactly how to take that throne.
Twenty years later, those three piano notes are embedded in the brains of anyone who’s ever come near a radio; Max Martin has left an impact on pop that rivals any studio auteur of prior generations; and Britney is still Britney, bitch. And us? Well, we still believe (still believe!). — J. Lynch