If you entered 2000 thinking that the year would bring a totally different sound befitting the turn of a new millennium... well, you were mostly right.

Not that the artists that defined popular music at the end of the '90s were suddenly spirited away and replaced with an entirely new vanguard: Most of the biggest artists of 1999 -- the boy bands and girl groups, the breakout rappers and rock best-sellers -- were the biggest artists of 2000, too. But they seemed energized by the changeover of millennia, and motivated to push things appropriately forward.

Having some of the era's greatest super-producers on the front lines certainly helped. Timbaland and Rodney "Darkchild" Jerkins amped up the dramatic tension of R&B until it sounded like something that would play at a futuristic opera. The Neptunes and Swizz Beatz brought the proverbial (and sometimes literal) bells and whistles to hip-hop, setting it on its path to top 40 domination and definition. And of course, Max Martin raised the stakes on TRL pop, maturing his sound and proving that the genre and its greatest practitioners would not be left in the '90s with Trapper Keepers and Tamagotchis.

But the year wasn't just about returning '90s stars getting 2.0 updates. Hip-hop's geographical axis was thrown off by a brand new rap icon emerging from the country's center. R&B was modernized not only at its poppiest but also at its rootsiest, as the growing neo-soul movement experienced its greatest year of commercial and critical success. And a couple '80s stars returned with dramatically overhauled sounds that demonstrated they would be staying relevant well into their third decades.

With *NSYNC's No Strings Attached, a standard-setting 2000 pop release both in its cutting-edge production and its record-breaking commercial performance, celebrating its 20th anniversary -- and most of us needing no excuse to take a vacation from the world in 2020 -- Billboard decided the time was right for a week's celebration of the year 2000. We're starting today with a list of our 100 favorite songs from the historically rich year, and will continue all week with a series of essays, interviews, lists and other flashbacks to the beginning of the new millennium.

First, though, a note about eligibility: Songs were counted as eligible if they were released as singles in '00, if they debuted on the Billboard charts in '00, or if they hit No. 1 in '00. But if they didn't hit the Hot 100 until the next year, or if they debuted in '00 but didn't hit No. 1 until the year after, we're counting 'em for '01. So apologies to "Ms. Jackson," "It Wasn't Me," "Yellow," "One Step Closer" and "One More Time" -- we'll probably see them on this list next year.

Read our list below, find a Spotify playlist of all songs at the bottom, and check back to Billboard.com all week for more about the stories behind the most interesting songs and albums of 2000. It's been a long time since they left you -- so begin the journey back with us below, with 100 dope jams to step to.

100. Zombie Nation, "Kernkraft 400" (Sport Chant Stadium Remix) (No. 99, Hot 100)

By the end of the '90s, music for video games and music for sporting events had starting overlapping to the point of being interchangeable -- so it made sense that one of the ultimate mind-numbing dance anthems at the turn of the millennium should be a remix of a video game theme with a soccer chant stapled on top of it. Call it "Seven-Bit Nation Army," with fewer distracting verses. -- ANDREW UNTERBERGER

99. P!nk, "There You Go" (No. 7, Hot 100)

Long before we knew her as the acrobatic performance-loving pop star, P!nk was introduced to the world as the next R&B artist to watch with breakout single “There You Go.” Due to its swagger-heavy production and soulful vocals, many thought the singer was actually a light-skinned black girl. That wasn’t the case, of course, but P!nk made it clear that she’d never fit into the bubblegum-pop mold of Y2K and beyond. -- BIANCA GRACIE

98. O-Town, "Liquid Dreams" (No. 10, Hot 100)

If you need a reminder of who was hot in 2000, press play on O-Town’s “Liquid Dreams.” Destiny’s Child, Madonna, Janet Jackson, Angelina Jolie, Cindy Crawford, Tyra Banks and Salma Hayek all get shout-outs in the zeitgeist-y hit (as well as a mysterious reference to “Jennifer” in the chorus -- Lopez? Aniston? Love Hewitt?). Its snapping beat and rolling melody made for a dynamic debut from O-Town, the first product of Diddy’s artist-scouting series Making the Band, reaching the Hot 100's top 10. Perhaps the most ingenious part of “Liquid Dreams,” though? It’s so catchy, you forget they're singing about a wet dream. -- TAYLOR WEATHERBY

97. The White Stripes, "Hello Operator" (Did not chart)

In a year when rock leaned into "nu" strains by bands like Limp Bizkit and Linkin Park, The White Stripes sounded refreshingly, well, old. On their sophomore LP De Stijl, the Detroit duo extended the garage rock blues of their eponymous 1999 debut, and while De Stijl was stacked with eventual classics, none were as raucously, righteously dirty as "Hello Operator." Here Jack's guitar sounds hot to the touch, while Meg's drums deliver a skeletal interlude to the otherwise headbanging track -- which in just 2:36 demonstrated that 20th century-style rock was alive and thrashing in the nu millennium. -- KATIE BAIN

96. Toby Keith, "How Do You Like Me Now?!" (No. 31, Hot 100)

Seven years after "Should've Been a Cowboy," Toby Keith rebounded from a stretch of stalled singles and reclaimed his mid '90s dominance with a honky tonk send-off to the it-girl valedictorian who never gave him the time of day. High school Toby's tactics were sure questionable ("Broke into the stadium and I wrote your number on the 50-yard line") but his hooks are anything but; when the chorus hits, it sails through the goalposts. -- CHRIS PAYNE

95. Mandy Moore, "I Wanna Be With You" (No. 24, Hot 100)

Mandy Moore was only 16 when she released the single that would become her biggest Hot 100 hit, and in many ways it sounds like it: a wispy ballad of teenage longing, not all that far removed from Jessica Simpson's contemporaneous "I Wanna Love You Forever." But there's both a tenderness and a yearning to "I Wanna Be With You" that hints at a maturity that would manifest in Moore's later singer-songwriter work; with its sighing and soft-hearted lustfulness, it's something like a TRL-era "Wouldn't It Be Nice." -- A.U.

94. Black Rob, "Whoa!" (No. 43, Hot 100)

Though The Notorious B.I.G. and Ma$e were considered pillars for Diddy's Bad Boy conglomerate in the '90s, Puff bolstered his decorated lineup when he recruited Harlem lyricist Black Rob in 1997. In 2000, Rob Marciano returned the favor and swung for the fences with his war-ready single "Whoa!" Teeming with grit and swagger, "Whoa!" was a pure New York banger, which spoke to the high degrees of flexing. -- CARL LAMARRE

93. The Dandy Warhols, "Bohemian Like You" (No. 28, Alternative Songs)

There’s something deeply self-referential about an alternative band like The Dandy Warhols penning an unforgettable (and popular) track about the hypocrisy of hipster culture. Getting used in popular commercials of the day and becoming their biggest hit to date, “Bohemian Like You” paints a crystal-clear picture of the pseudo-counter-culturalism that came to define the later decade, and made minor stars out of the alt-rockers behind it. -- STEPHEN DAW

92. Miss Kittin & The Hacker, "Frank Sinatra" (Did not chart)

With the blasé ennui of Marlene Dietrich, French electroclash pioneer Miss Kittin recounts the salacious late-night deeds of the late Rat Packer over a frangible beat as icy cold as his remains. The blunt, brazen humor of "Frank Sinatra" ensures its cult longevity; even if the genre in question would soon become a stranger in the nightlife scene, its fetishized repurposing of synth-pop and '90s house would continue as a trend in dance until, well, now. -- JOE LYNCH

91. Hanson, "This Time Around" (No. 20, Hot 100)

Better known as Hanson’s “We’re adults now!” single, the title track to the brothers’ 2000 album had the unenviable task of following up their mega-selling 1997 LP Middle of Nowhere, as well as convincing pop listeners that the precocious voices behind “MMMBop” could credibly mature. “This Time Around” wasn’t a huge hit, but endures as first-rate pop-rock, with a piano line and a sing-along chorus that previewed Hanson’s fate as underrated adult songwriters, never to return to their early radio heights. -- JASON LIPSHUTZ

90. PJ Harvey, "Good Fortune" (Did not chart)

“Good Fortune” marked a sea change for PJ Harvey. The lead single off Stories from the City, Stories from the Sea rolls along with a quick tempo, lovelorn lyrics, and a sticky melody throughout, separating itself from the darkness of Is This Desire? and the knotty arrangements of To Bring You My Love. "Good Fortune” pre-dates fellow '90s alt sensation Liz Phair’s brazen 2003 crossover hit “Why Can’t I?” but Harvey’s unabashed daydream struck a balance that only she can, still unrecognizable to radio programmers and so individually PJ Harvey. -- ERIC FRANKENBERG

89. 2Gether, "The Hardest Part About Breaking Up (Is Getting Back Your Stuff)" (No. 87, Hot 100)

An impossibly on-point faux TRL jam -- down to the fake fans raving about their favs in the video's corner -- "Hardest Part" so nailed the boy-band breakup banger that you'd expect Max Martin and Rami Yacoub's names to pop up in the CD single liner notes. (Co-writers Brian Kierulf and Joshua M. Schwartz did end up on a number of songs on Britney Spears' 2001 Britney album.) The lyrics are inspired, of course, but the real highlights are the ad libs -- like the strangled "meow!" that follows the chorus' "You got my sweaters, my hat/ I can't find my cat!"-- A.U.

88. Delerium feat. Sarah McLachlan, "Silence" (No. 6, Dance Club Songs)

Before Sarah McLachlan made TV viewers scramble for the remote whenever the ASPCA's heart-wrenching ad with her "Angel" aired, she was tugging at heartstrings not only as a successful solo artist, but as a guest vocalist for new age/electronic outfit Delerium. The side project of Front Line Assembly’s Bill Leeb and Rhys Fulber reached new heights with McLachlan’s pipes on “Silence,” combining her dreamy vocals with Gregorian chants and a catchy beat. It's endured over the years with club-slaying remixes -- most notably Tiesto's epic In Search of Sunrise edit -- and today, echoes of the single’s dark and ethereal influence can be heard on Grimes’ recent Miss Anthropocene LP. -- ANNA CHAN

87. Hoku, "Another Dumb Blonde" (No. 27, Hot 100)

At a time when fresh-faced female pop stars were luring suitors with sexed-up schoolgirl outfits and genie metaphors, Hawaiian 18-year-old Hoku shook things up with her debut single, serving a “get lost” declaration to the players of the world. “Another Dumb Blonde” is feisty from start to finish, calling out a shallow jerk for being, well, just that (“Lately I’ve come to find/ That you're not really interested in my heart or mind,” proclaims the first pre-chorus). The spirited tune turned the blonde stereotype into an empowering anthem to brokenhearted tweens and teens everywhere -- no matter their hair color. -- T.W.

86. Jagged Edge, "Let's Get Married" (No. 11, Hot 100)

Since its release in February 2000, “Let’s Get Married” has been claimed by fans as a wedding anthem. Jagged Edge’s enduring ballad pushes all of R&B’s hot buttons: Silky harmonies. Smooth, body-rockin’ rhythms. Urgent heartfelt lyrics about true love. During its heyday, “Married" reached No. 1 on Hot R&B/Hip-Hop Songs and No. 11 on the Hot 100 -- aided by a popular Run-D.M.C.-sampling remix that also featured the group's Reverend Run. At a time when romantic love has increasingly become supplanted by records focusing solely on sex, people still desire songs that go all the way -- to lifelong commitment. -- GAIL MITCHELL

85. Ricky Martin, "She Bangs" (No. 12, Hot 100)

By the time "She Bangs" was released as the lead single to sophomore English-language LP Sound Loaded in October 2000, Ricky Martin was a bonafide hitmaker, with seven Hot 100 hits already to his credit. The danceable track meshed a salsa flare with heavy rock guitar and an irresistible pop beat for universal appeal, sending it to the top 20 on the Hot 100 and the top five in eight countries outside of the U.S. -- though its most memorable impact, for better or worse, may have come via future American Idol contestant William Hung. -- TAYLOR MIMS

84. Beenie Man feat. Mya, "Girls Dem Sugar" (No. 54, Hot 100)

Beenie Man already broke through the American market two years prior with the rugged dancehall crossover "Who Am I (Sim Simma).” But as he got more comfortable stateside, he decided to expand his sonic boundaries. And who better to help execute than The Neptunes? Dissecting a portion of “Who Am I,” the experimental duo transformed the original into a glossy, scratch-heavy club anthem that was elevated by Mýa’s dreamy "If I could be your girl...." coos. -- B.G.

83. Carlos Vives, "Fruta Fresca" (No. 1, Latin Songs)

Vives' lead single off El Amor de Mi Tierra (1999) shook traditionalists as it topped Latin Songs early in the new millennium. The Emilio Estefan- and Juan Vicente Zambrano-produced tune of swirling vallenato and pop pulsations revolutionized Latin music, without compromising Vives’ artistic integrity. Cannily structured, “Fruta” opens with enigmatic electro-acoustic guitar chords, followed by Vives' vigorous vocals and flanked by sturdy bass and percussion; reflecting the turn of a genre that slinked smoothly into its own space. Vives deftly weaved Colombia’s popular folk music with Latin pop -- belted by bouncy accordion, along with caja and guacharaca -- and became a leading figure in the mainstream tropical sphere. -- PAMELA BUSTIOS

82. Limp Bizkit, "Break Stuff" (No. 14, Alternative Songs)

For those of us who lived through the turn-of-the-century nu-metal heyday, all it takes is that chunky two-chord riff from Wes Borland that opens Limp Bizkit’s “Break Stuff” to get us nice and furious. The Significant Other single is designed for mosh pits -- after all, it climaxes with Fred Durst screaming “Give me something to break!” -- and captures a relic of the era at its biggest, dumbest and best. -- J. Lipshutz

81. Carl Thomas, "I Wish" (No. 20, Hot 100)

Plenty of great R&B torch songs have dealt with unrequited love over the years, but few besides Bad Boy belter Carl Thomas' "I Wish" have so lamented a love that was requited: "I love her so, she's got love for me/ But she still belongs to someone else." The unusual heartbreak ballad was saved from maudlinism by a breezy, piano-led Mike City production and a crescendoing vocal performance from Thomas that was absolutely superlative -- though that didn't stop Jay-Z and the rest of us from our own off-key imitations: "And I wish... I neeever... met herrrr... at alll..." -- A.U.

80. 3LW, "No More (Baby I'ma Do Right)" (No. 23, Hot 100)

These 3 Little Women had some big boy problems, given all those mysterious numbers lighting up their boo's pager. But the trio of ladies -- with the youngest member only 14 years old (hence the reference to "last year, boy, in the eighth grade") -- aren't putting up with any more, and they make it super clear with this exasperated-but-catchy musical kiss-off. -- KATIE ATKINSON

79. Sting feat. Cheb Mami, "Desert Rose" (No. 17, Hot 100)

Fifteen years into his lucrative post-Police solo career, Sting had the freedom to do pretty much whatever he wanted. So when his globetrotting dreams had him pining for love's eternal salvation amongst "gardens in the desert sand," well, that's exactly where he went. With the bombast of a Disney musical and all Pure Moods editions combined, "Desert Rose" was a portal for every minivan in America to some enchanted sonic oasis. Or if you were Sting in the track's product-placement-addled video, a chauffeured journey in a 2001 Jaguar S-Type through the Mojave Desert, to meet Algerian wailer Cheb Mami at a top-secret disco rendezvous. -- C.P.

78. Kylie Minogue, "Spinning Around" (Did not chart)

While some saw a new millennium as an opportunity to create music unlike anything anyone had ever heard before, Australian superstar Kylie Minogue took a different approach. With “Spinning Around,” the songstress nailed the classic, disco-inspired Europop sound that would carry her into the 21st century, and went on to see massive success just about everywhere (except America, which sadly would take a couple more years to catch on). The track’s danceable melodies and irresistible beat proved that all spinning aside, you don’t have to reinvent the wheel to show people a good time. -- S.D.

77. Samantha Mumba, "Gotta Tell You" (No. 4, Hot 100)

That Samantha Mumba has released, to date, one album remains one of pop’s biggest recent-ish tragedies. That’s because Gotta Tell You is a debut LP armed to the teeth with bubblegum pop bangers -- and the title track in particular, her debut single, exudes a soulful confidence well beyond Mumba’s then-17 years, and boasts a whopper of a minor-key chorus. Bonus points always and forever given to the front flip off a store awning into a choreographed dance Mumba pulls off (OK, OK, through the magic of editing) in the video. -- KEVIN RUTHERFORD

76. The Baha Men, "Who Let the Dogs Out?" (No. 40, Hot 100)

In life, there are a handful of questions that humanity has struggled to definitively answer: did the chicken or the egg come first? How many licks does it take to get to the center of a Tootsie Pop? And who, indeed, let the dogs out? But some mysteries are better left unsolved, and though we still haven’t found the culprit two decades later, that shouldn’t stop us from queueing back up the can’t-miss, Grammy-winning (?) stadium anthem and letting out a “yippie, yi, yo!” or two. While remaining vigilant. -- JOSH GLICKSMAN

75. Erykah Badu, "Bag Lady" (No. 6, Hot 100)

Badu’s soulful classic about letting go of emotional baggage is basically a mini-therapy session, thanks to its soothing, tonic-like beat and timeless wisdom (“All you must hold onto is you,” she advises in effortless croon). Meanwhile, a twangy sample from Dr. Dre’s “Xxplosive” adds a subtle flourish to the otherwise minimal sound. The song picked up two Grammy nominations and peaked at No. 6 on the Hot 100, making it Badu’s highest-charting track to this day. -- TATIANA CIRISANO

74. Air, "Playground Love" (No. 28, Dance Singles Sales)

With its dream-pop melodies and soothing vocals, Air's "Playground Love" may have been released in 2000, but it can easily transport fans back to the '70s. "I'm a high school lover and you're my favorite flavor," the lyrics begin, a hopeless romantic penning their deepest feelings. As part of the Me Decade-set soundtrack to Sofia Coppola's lovelorn and ultimately tragic The Virgin Suicides, there's no doubt that "Playground Love" continued to mold a new generation of sentimental high school sweethearts -- as well as those to follow. -- JESSICA ROIZ

73. Janet Jackson, "Doesn't Really Matter" (No. 1, Hot 100)

There’s something lovely about watching an outwardly beautiful Janet Jackson sing about inner beauty. While playing the romantic interest of a fat suit-wearing Eddie Murphy in the Nutty Professor II: The Klumps, the pop icon co-penned the breathy single for the rom-com's soundtrack (with longtime producers Jimmy Jam and Terry Lewis) about a love that's blind and strong enough to withstand the haters. Set in futuristic Tokyo, the video for the sultry, sighing dance track is the song’s final punctuation mark -- featuring sparkly gadgets, a robot dog and a dance break on a levitating platform -- helping the song become her first Hot 100-topper of the 2000s. Clearly, it “Doesn’t Really Matter” the decade, Ms. Jackson is timeless. -- DANICA DANIEL

72. Deftones, "Change (In the House of Flies)" (No. 3, Alternative Songs)

Taking place over various stages of a seedy Hollywood party that always seems on the precipice of something truly terrible happening, the video for the Deftones' biggest hit captures its feeling perfectly: mysterious, beautiful, seductive and imminently perilous. Croaked by frontman Chino Moreno as if from the bottom of the house's swimming pool, "Change" was a version of nu-metal horror that eschewed jump scares for unnerving suggestion; it had only a fraction the pop impact of Limp Bizkit, but remains exponentially more unshakeable 20 years later. -- A.U.

71. Savage Garden, "I Knew I Loved You" (No. 1, Hot 100)

Savage Garden was one of those bands that seemed disproportionately popular in Southeast Asia (see also: Westlife). In the Philippines, people love ballads and karaoke, so the sentimental “I Knew I Loved You” was an irresistible choice for radio DJs, weddings, and any instance in which Filipinos can sing with feelings. "Loved" was also universal enough to become the duo's second No. 1 hit on the Hot 100 -- and the music video was just as good, featuring vocalist Darren Hayes reaching for Kirsten Dunst to hold hands on a subway. -- MIA NAZARENO

70. Fuel, "Hemorrhage (In My Hands)" (No. 30, Hot 100)

Two decades years after its heyday, it's crazy to think that Fuel's "Hemorrhage" could have been a massive hit on pop radio (reaching No. 22) at any point this century, even making the top 40 of the Hot 100, as pop and hip-hop flood today's charts. But Fuel did just that with their crossover post-grunge ballad "Hemorrhage (In My Hands)," in which frontman Carl Bell sings about his grandmother's cancer diagnosis and eventual passing. Of course, the powerful singalong with a massive chorus -- whether you knew what it was about or not -- was also massive staple on rock radio, spending a staggering 12 weeks at No. 1 on Billboard's Alternative Songs chart. -- XANDER ZELLNER

69. Incubus, "Stellar" (No. 2, Alternative Songs)

The only way to understand Incubus within the nu-metal rock world of 2000 is to follow singer Brandon Boyd’s guidance at the opening of their celestial single “Stellar”: “Meet me in outer space.” The enigmatic five-piece presented a new, surrealist vision for the exploding genre, with the song’s serpentine melody disguising math-rock as metal and its distortion-heavy chorus belying the cuddly love song at its core. “Stellar” proved to have a lasting impact as the mainstream rock renaissance began to wane, partially thanks to its embrace by the younger Guitar Hero generation. -- BRYAN KRESS

68. Marc Anthony, "You Sang to Me" (No. 2, Hot 100)

Twenty years later, this song should still come with a warning about listening when you're feeling vulnerable. There's just no pretense with "You Sang to Me," a breathtaking vista of a ballad that sounds gorgeous and heartbreaking. The song was patently massive -- it peaked at No. 2 on the Hot 100 and topped the Adult Contemporary chart for seven weeks -- but its heart and soul lies in its subtle sentimental brushstrokes: the weeping acoustic guitars, the stately accordion solo, Anthony's stirring a cappella coda: "OHHHH BUT I FEEL IT." The feeling's mutual. -- C.P.

67. Toni Braxton, "He Wasn't Man Enough" (No. 2, Hot 100)

After steamrolling through the 1990s with a barrage of top 40 and adult contemporary mainstays, Toni Braxton returned in March of 2000 with “He Wasn’t Man Enough.” It’s an upbeat Darkchild production that was right at home on pop and R&B radio in the aftermath of similar-themed hits by TLC (“No Scrubs”) and Destiny’s Child (pretty much everything they’d released to that point). And while the song begins with Braxton looking down on her ex’s new boo, her condescension turns to thoughtful protectiveness. This femme-forward approach is highlighted by the finale of the music video -- which, from the styling to the Y2K-futurist lighting and set design, could not be more 2000. -- E.F.

66. David Gray, "Babylon" (No. 57, Hot 100)

“Let go of your heart, let go of your head and feel it now” commands the chorus of David Gray’s “Babylon.” The warm and melancholic folk song (and second single from Gray's breakout album White Ladder) became the singer-songwriter's signature track at the turn of the millennium. Laden with harmonious flurries, Gray’s vocals dance over the melody and hit your ears with force. There is a general feeling of surrender, of letting loose to pick up the mess of a relationship that is vanishing in Gray's native London -- considered a modern-day Babylon in Victorian times -- that ricochet between the subtly tech-aided melody and the shrewd wit of his lyrics. -- P.B.

65. BBMak, "Back Here" (No. 13, Hot 100)

British trio BBMak arrived at the height of the boy band bonanza as a slight bit of counter programming -- sure, they were pretty and harmonized, but they played instruments, too! Yet the perception of authenticity is irrelevant to the quality of “Back Here,” a soft, gorgeous pop track with one of the most delicate bridges of the teen-pop era; it peaked at No. 13 on the Hot 100 chart, but has remained a charming staple of adult contemporary radio for decades. -- J. Lipshutz

64. Madonna, "Don't Tell Me" (No. 4, Hot 100)

Throughout her career, Madonna has often followed her flashy lead single from a new album with something more curious and subtle, yet no less rewarding as the follow-up. Such was the case for her Music era, in which the title track offered electro-pop euphoria, before second single “Don’t Tell Me” served as an act of twangy defiance -- with clipped vocals, guitar loops, strings and a mainstream take on folktronica that still holds up today. -- J. Lipshutz

63. Peaches, "F--k the Pain Away" (Did not chart)

Before Cupcakke, before “My Neck, My Back,” and before the advent of iTunes and streaming services made FCC radio standards more or less obsolete, there was “F--k the Pain Away,” a song so proudly explicit that it became something of a proto-meme. But it’s also just an excellent song, frank and minimalistic, anchored by buzzing bass and percussive claps. It’s a testament to Peaches’ vision that, 20 years on, her breathless enjoinder feels so distinctly of the moment. -- WILL GOTTSEGEN

62. SR-71, "Right Now" (No. 2, Alternative Songs)

The debut single from SR-71, “Right Now” embodies the classic pop-punk sound that exploded at the dawn of the 21st century. It quickly cemented itself in pop culture, being used in the trailer and soundtrack for Dude, Where's My Car? and going on to become something of a stoner movie staple, later also being featured in the 2004 trailer for Harold & Kumar Go to White Castle. From the unforgettable opening riff to the solid mid-song guitar solo to the “Bohemian Rhapsody” nod in the video, it's a song that will exude nostalgia forever. -- BECKY KAMINSKY

61. Aaron Carter, "Aaron's Party (Come Get It)" (No. 35, Hot 100)

Before life was unkind to Aaron Carter, we had his party, and it was glorious. Here's a little bit of old school for ya: It’s the year 2000, and Nick Carter’s little bro is making a name for himself through funky, guitar-driven pop-rap. It’s a simpler time, when the worst possible punishment a kid can get is to be grounded -- and that’s just what Aaron's in for once his parents find out about the house party he threw when they were out. (Don’t worry, attendees were only served juice.) As the title track of Carter's 3x platinum second studio album, “Aaron's Party” was released when he was just 12 years old, and its witty lyrics, charming video and equally adorable star ensure it’ll be a tale for the ages. -- GAB GINSBERG

60. Enrique Iglesias, "Be With You" (No. 1, Hot 100)

Enrique Iglesias’ “Be With You” became his second No. 1 on Billboard’s Hot 100, after “Bailamos,” and ruled the chart for three weeks. This timeless song, which has a heartbroken Enrique yearning to get back with his girl, has become a classic because it was part of the Spanish singer’s eponymous 1999 bilingual album – his formal introduction to mainstream America, with which he won over hearts singing in English – and thanks to his soaring “Now that you're gone/ I just wanna be with you” hook. -- GRISELDA FLORES

59. At the Drive-In, "One Armed Scissor" (No. 26, Alternative Songs)

“One Armed Scissor” is full of dissonance -- whether it’s Cedric Bixler-Zavala’s sometimes-barked vocals and its juxtaposition against Jim Ward’s Warped Tour-ready chorus howl, its jarring time signature changes, Ward and Omar Rodriguez-Lopez’s snaking guitar riffs, or its hair-raising refrain of “Get away! Get away!” Perhaps the song’s multiple moving parts, somehow joining together in a cohesive package amid its 4:20 run time, were a harbinger of At the Drive-In’s demise less than a year later, then at the height of its popularity. -- K.R.

58. No Doubt, "Simple Kind of Life" (No. 38, Hot 100)

After the take-no-prisoners confidence of Tragic Kingdom's "Just a Girl" made Gwen Stefani a star, the exquisite second single from No Doubt's sophomore LP Return of Saturn revealed the second-guessing she'd undergone in the years since -- wondering if despite the magazine covers and diamond-certified sales, she was more suited the titular existence. It's a heartbreak song where the she's the victim not of a bad boyfriend (she had recently started seeing Bush's Gavin Rossdale), but of a successful career, one that leaves her hoping for an accidental pregnancy to take the decision out of her hands. "You seem like you'd be a good dad" never sounded so devastating. -- A.U.

57. Ja Rule feat. Lil Mo & Vita, "Put It on Me" (No. 8, Hot 100)

Though Ja Rule and Vita left their handprints on the Rule 3:36 album version for "Put It on Me," it was Lil Mo's soaring ad-libs that drove the song's remix towards mainstream notoriety. A quintessential ride-or-die anthem, "Put It on Me" (Remix) not only made Ja Rule's howling croons a much-needed staple in hip-hop, but gave him credibility as a promising hitmaker in the 2000s. -- C.L.

56. Mya, "Case of the Ex (Whatcha Gonna Do)" (No. 2, Hot 100)

Mýa was always good for masking petty digs in sweet tunes (see 1998’s “Movin’ On”), but she entered her final form with the sharp-tongued “Case of the Ex.” Our R&B darling was completely fed up with her man communicating with a past fling -- “There's no need to reminisce 'bout the past/ Obviously, cause that s--t did not last” -- and Tricky Stewart’s spiny production drove her frustration over the edge. And the ladies related: by Y2K’s end, “Case of the Ex” leaped to No. 2 on the Billboard Hot 100. -- B.G.

55. Common, "The Light" (No. 44, Hot 100)

In the bleak, aggressively macho hip-hop landscape of the early '00s, Common followed his own luminescence. Taken from his breakthrough major label debut Like Water For Chocolate, “The Light” feels transported from the conscious rap heyday of the '90s with chivalrous rhymes that read like stanzas in a love poem -- appropriate for the song's written-letter framing. Inspired by then-flame Erykah Badu, produced by J Dilla (sampling Bobby Caldwell deep cuts), and influenced by the nascent neo-soul sound of the Soulquarians, “The Light” presents the brighter side to a rap scene in flux. -- B. Kress

54. SoulDecision feat. Thrust, "Faded" (No. 22, Hot 100)

In the midst of the boy-band craze, this Canadian five-piece snuck a disco-pop hit into the Hot 100's top 40, thanks in part to their Brad Pitt-look-alike frontman and his era-appropriate frosted tips fitting in perfectly with the TRL aesthetic. This gem has been sort of lost to time -- sadly, it's not even currently available on streaming services -- but its funky bass line and cheekily provocative lyrics deserve to be remembered. -- K.A.

53. Creed, "With Arms Wide Open" (No. 1, Hot 100)

In no uncertain terms, Creed perfected the post-grunge mid-tempo ballad, and “With Arms Wide Open” is its greatest such creation. Skip the various radio versions (strings or no strings), which tip the melodrama in too precarious a direction; it’s already impassioned enough as is, thanks to Scott Stapp’s musings on the surprise of learning he’d soon become a father. Side note: Creed’s 1999 mission statement release, Human Clay, features this song and “Higher” back to back at track Nos. 7 and 8 – way to bury the lede, guys! -- K.R.

52. Dream, "He Loves U Not" (No. 2, Hot 100)

Dream’s debut album may have been called It Was All a Dream, but this fearsome foursome was not reading Word Up! Magazine. Signed to Puff Daddy’s Bad Boy Records, the girl group made slickly produced pop R&B and found its biggest success with “He Loves U Not,” a funky tell-off wherein the singers are so confident in their man’s loyalty that they dare another female to go ahead and try to steal him. The sassy cut came with an equally self-assured video, complete with finger-wagging, matching pearly pink outfits and dune buggy rides in the desert. -- CHRISTINE WERTHMAN

51. Green Day, "Minority" (No. 1, Alternative Songs)

Don’t be fooled by the opening moments of easygoing acoustic guitar -- this Warning lead single quickly delves into a rebellious, rollicking call to embrace individuality, with intermittent harmonica and accordion providing both a change of pace and some western European flair along the way. “Minority” wouldn’t serve to be Green Day’s last (or most notable) politically themed hit, but it’s nevertheless hard to resist throwing up two middle fingers alongside Billie Joe Armstrong as he yells “f–k ‘em all” in the lead up to the chorus. -- J.G.

50. Bloodhound Gang, "The Bad Touch" (No. 52, Hot 100)

In 2000, no radio hit was stranger, hornier or catchier than "The Bad Touch." An homage to mating by Pennsylvania-bred rock act Bloodhound Gang, the song amalgamated spoken-word lyrics, NSFW themes, funk guitar and club production into a crossover hit that peaked just outside the Hot 100's top half. Packed with pop culture references -- Siskel & Ebert! Prince! The X Files! -- and joyfully stupid double entendres, the shelf life of the unexpected hit was extended when Eminem referenced it in his smash "The Real Slim Shady" later that year. -- K.B.

49. Son by Four, "A Puro Dolor" (No. 26, Hot 100)

A true classic in Latin pop culture, Son By Four's "A Puro Dolor" puts in perspective unconditional love, a heartbreak, and the horrible feeling of missing someone. "Give me back my fantasies and the courage I need to live," the group expresses in the heartfelt lyrics. The ballad was such a hit that there were three versions of the song on the group's self-titled album -- also including English and Salsa versions -- making it a true timeless gem. In addition to making the Hot 100's top 40, “A Puro Dolor” topped the Hot Latin Songs chart in April 2000, reigning for a then-record 20 weeks. -- J.R.

48. Third Eye Blind, "Never Let You Go" (No. 14, Hot 100)

Between 1997 and 2000, there was no bigger pop-rock act in the world than Third Eye Blind. Fresh off three mega-hits off their self-titled debut, which all reached the top 10 of the Hot 100, the group's standout single from their second LP Blue managed to surpass all of them (well, except "Semi-Charmed Life") in pop-culture longevity. Sandwiched between a recognizable opening guitar riff and an anthemic, albeit cheesy, spoken-word ending, Stephan Jenkins sings about a relationship that's doomed to end, but he just can't come to terms with it. Decades years later, that angst still resonates, and its legacy even prompted a recent cover from RAC and Hilary Duff. -- X.Z.

47. Lonestar, "Amazed" (No. 1, Hot 100)

One of the modern country's greatest love songs proved its power with how it impacted two of its songwriters. Surrounded by candlelight, Aimee Mayo, Chris Lindsey and Marv Green penned “Amazed,” which was released as the second single off Lonestar’s third studio album Lonely Grill. “Amazed” immediately shot to No. 1 on Billboard's Hot Country Songs chart, where it would stay for eight weeks -- and Mayo and Lindsey later married. The heart-tugging power ballad, with lyrics like “I want to spend the rest of my life, with you by my side,” continues to be one of the world’s most popular wedding songs, putting us in the mood to fall in love “forever and ever” even when there's no aisle in sight. -- D.D.

46. Red Hot Chili Peppers, "Otherside" (No. 14, Hot 100)

Red Hot Chili Peppers are not a band known for their harmonies per se, but the best moments in “Otherside” prove that the vocal pairing of frontman Anthony Kiedis and on-again, off-again guitarist/backing vocalist John Frusciante can be a winning one. The beauty of their melding voices on the chorus is fitting with the gravity of the song’s subject matter: a tribute to fallen guitarist Hillel Slovak, who died of a heroin overdose a decade earlier, along with Kiedis and Frusciante’s own struggles with addiction. Honorable mention, too, to one of Flea’s most melodic, memorable basslines in a career full of them. -- K.R.

45. Vitamin C, "Graduation (Friends Forever)" (No. 38, Hot 100)

If you’ve been to a middle or high school graduation in the past 20 years, you’ve likely watched a choir of awkward, brace-faced teenagers sing the unmistakable chorus of Vitamin C's commencement anthem. Using a melodic interpolation from the classical convocation staple, Pachelbel’s "Canon In D" -- and matched with lyrics pondering if Heather can "find a job that won't interfere with her tan" -- "Graduation" has given us a soundtrack to the bittersweet uncertainty of graduation, with a fresh, pop twist that feels more innocently nostalgic and much less stuffy. -- RANIA ANIFTOS

44. Radiohead, "Optimistic" (No. 10, Alternative Songs)

“You can try the best you can/ The best you can is good enough” is a sweet sentiment on the surface, but it carries a beguiling menace as the chorus of Radiohead’s dystopian anti-capitalist anthem. The only radio hit off the landmark Kid A album, “Optimistic” trades in any actual positivity for unnerving sarcasm: Instead of closing the song with a final refrain of “the best you can is good enough,” we’re left with the haunting prophecy (or realization) that try as best we might, dinosaurs are more likely to roam the earth than our optimism coming to fruition. Happy quarantining everyone! -- E.F.

43. LeAnn Rimes, "Can't Fight the Moonlight" (No. 11, Hot 100)

The theme song to a movie no teen's parents really wanted them to see, "Can't Fight the Moonlight" boasts a sing-it-to-the-constellation chorus courtesy of widescreen song-scribe Diane Warren, and scuzz-lite production from studio vet/Buggles frontman Trevor Horn. But what takes this Coyote Ugly cut from happy hour to top-shelf status are LeAnn Rimes' versatile vocals, which weave between peated-whisky lows and sugary Prosecco highs, with the deft craftsmanship of a bartender who abstains while everyone around keeps knocking 'em back. -- J. Lynch

42. The Avalanches, "Since I Left You" (Did not chart)

Like so much of Australian electronic outfit The Avalanches’ best music, “Since I Left You" (off their 2000 album of the same name) is as lighthearted and whimsical as it is quietly experimental. It’s a psychedelic collage of pop sounds, with samples of everything from pitched-up soul to warped jazz guitar mixed into a celebratory jam -- one that masks the pain of heartbreak with hope and humor. A dizzying pastel universe, with nothing but new horizons. -- W.G.

41. Vertical Horizon, "Everything You Want" (No. 1, Hot 100)

How did “Everything You Want,” a relatively understated alternative rock single from Vertical Horizon, reach the top of the Hot 100 chart in July 2000? Well, few alternative rock singles from that era were as emotionally affecting as “Everything You Want,” in which frontman Matt Scannell sings about an inexplicable absence of love a woman feels toward a man, before flipping the final chorus and making the man himself. Meanwhile, the bobbing guitar line creates a sense of unsteadiness, creating a sense of frustration that explodes into one of the strongest choruses of the year. -- J. Lipshutz

40. Christina Aguilera, "Come on Over Baby (All I Want Is You)" (No. 1, Hot 100)

In 1999, Christina Aguilera dropped her self-titled debut album, and solidified her place in the teen-pop kingdom. Her third single off the set, “Come On Over Baby (All I Want Is You),” was the upbeat, Radio Disney-approved bop that prompted a generation of girls to sing into their hair brushes during bedroom concerts. The hit song was danceable and addictive, becoming her third straight Hot 100 No. 1 and helping pave the way for the age-old debate: Christina or Britney? -- M.N.

39. U2, "Beautiful Day" (No. 21, Hot 100)

Given how unavoidable it became in early-'00s pop culture, it’s pretty surprising that “Beautiful Day” never cracked the Hot 100's top 20 -- and that its No. 21 peak barely edged out the highest ranking for American Idol winner Lee DeWyze’s 2010 cover. Regardless, U2's All That You Can’t Leave Behind lead single has stood the test of time, becoming a song of inspiration and hope in the process. Its uplifting message accompanied by its pulsing, eventually erupting backing begs for a frolic outside -- just remember to keep a safe social distance while doing so. -- J.G.

38. Jay-Z, "I Just Wanna Love U (Give It 2 Me)" (No. 11, Hot 100)

With its shimmying, infectious beat and playful verses from Jay-Z, “I Just Wanna Love U” became the rapper’s first No. 1 on the Hot R&B/Hip-Hop Songs chart, also reaching No. 11 on the Hot 100. But it wasn’t just a hit for Hov, as the song also boosted a commercial rise for The Neptunes -- who not only produced the track, with a chorus sung (uncredited) by Pharrell Williams in a soon-to-be-trademark falsetto, but got a shoutout from the man himself: "Profess yo' love to Hov, and I'll never let you down/ Get you bling like the Neptune sound." -- T.C.

37. Bon Jovi, "It's My Life" (No. 33, Hot 100)

By the release of their 2000 LP Crush, New Jersey stadium rock heartthrobs Bon Jovi had scored 15 years worth of hits, and had earned the right to be self-referential. And so Tommy and Gina, the working-class heroes from the band's 1986 signature smash "Livin' on a Prayer," were written into "It's My Life," Bon Jovi's comeback-singalong-air-guitar-power-anthem. Over a decade after the fictional couple first entered pop culture lore, "It's My Life" lauded the pair for never backing down -- as the similarly steadfast Jon Bon Jovi belted about livin' in the moment, and introduced a new generation to fist-pump rock at its finest. -- K.B.

36. Mystikal, "Shake Ya Ass" (No. 13, Hot 100)

At the dawn of the 21st century, No Limit soldier Mystikal came armed to the teeth in order to secure his first crossover hit as a lead artist. "Shake Ya Ass" not only boasted an typically irresistible Neptunes shuffle, but two knockout choruses commanding the titular instruction -- the first hurled by the lead NoLa carnival barker, and the second gently suggested by his sweet-falsetto'd VA hook man. Any worries that Mystikal's verses couldn't bring the thunder to match were put at bay by his opening couplet: "I came here with my d--k in my hand/ Don't make me leave here with my foot in yo' ass!" -- A.U.

35. Santana feat. The Product G&B, "Maria Maria" (No. 1, Hot 100)

As legend has it, Wyclef Jean got the idea for “Maria Maria” after listening to Wu-Tang Clan’s 1993 banger “Wu-Tang Clan Ain't Nuthing ta F' Wit.” Soon, the mastermind transformed that menacing riff into a summer anthem anchored by Santana’s Latin-infused guitar licks and The Product G&B’s honeyed croons. After topping the Hot 100 for 10 weeks and earning a Grammy, “Maria Maria” later returned to the charts' top tier when DJ Khaled sampled it for 2017’s “Wild Thoughts,” featuring Rihanna and Bryson Tiller. But nothing could compare to those seductive notes first played by Car-los San-ta-na. -- B.G.

34. Nine Days, "Absolutely (Story of a Girl)" (No. 6, Hot 100)

Remember when power pop songs used to go Top 10? In the year 2000, Nine Days' story of a girl -- the one who famously cried a river and drowned the whole world -- peaked at No. 6 on the Hot 100 due to that undeniable singalong chorus. While there is some debate as to whether the song is about lead vocalist/guitarist John Hampson’s then-girlfriend (and now wife) Teresa Savino, or a lesser-known ex, one thing’s for sure: the song about her winning smile still bangs. Plus, its legacy stays alive through TikTok, and in our Y2K pop-rock-loving hearts. -- G.G.

33. Backstreet Boys, "Shape of My Heart" (No. 9, Hot 100)

How do you top one of the greatest boy band songs of all time? Well, even the Backstreet Boys couldn’t best the magic of “I Want It That Way,” but they came pretty close to matching it with the lead single from their third LP, Black & Blue. From the second the guitar starts strumming, “Shape Of My Heart” has you in your feels, and that just keeps escalating as the song reaches its climactic belt-along chorus. Its lyrics and punchy production make “Shape Of My Heart” as charmingly cheesy as any BSB classic, and though the impassioned song couldn’t quite surpass "That Way," at least its message is a little clearer. -- T.W.

32. Alice Deejay, "Better Off Alone" (No. 27, Hot 100)

If ringtones weren't going to be a thing in the 2000s, they would've had to invent them just for the synth hook to "Better Off Alone"; the "(I Can't Get No) Satisfaction" of turn-of-the-millennium electro-pop. Blast it from the mountains, cry-dance to it in your bedroom, tap it out on your desk at the office -- it's a riff for all seasons, one that's become part of our cultural DNA, one that we can still feel in our bones 20 years later. And don't count out the vocal from Judith Pronk, which wrings an unthinkable amount of sympathy out of just ten words: "Do you think you're better off alone?/ Talk to me." -- A.U.

31. Britney Spears, "Lucky" (No. 23, Hot 100)

It may not be the first song you think of off of Oops!…I Did It Again, but Britney Spears’ “Lucky” is one of her greatest songs to date. “Lucky” saw Spears actually using her music to comment on the difficulties of being catapulted into the public eye and the isolation it causes, all while getting her fans to sing and dance along. Simultaneously heartbreaking and unbelievably campy, “Lucky” is Britney Spears at her most self-aware, even when it just sounds like a silly story about “a girl named Lucky.” -- S.D.

30. Lee Ann Womack, "I Hope You Dance" (No. 14, Hot 100)

This song won practically every award in the country music field for a good reason -- it's a touching ballad that doesn't come across as overly sweet or sentimental. The song isn't explicitly framed as a parent's wish for a child, though that's how most listeners interpret it. In recent popular culture, the only parental message that is as moving is the father's eloquent speech to his gay son in Call Me By Your Name. Gladys Knight, who knows a powerhouse piece of material when she hears one, covered the song in 2013, but the version that Womack recorded with Sons of the Desert remains definitive. -- PAUL GREIN

29. Wheatus, "Teenage Dirtbag" (No. 7, Alternative Songs)

At a time when cocky pop-punk bands ruled TRL, Brendan B. Brown’s band Wheatus offered a more self-effacing, though still rocking, alternative with its song for all the losers out there, “Teenage Dirtbag.” Brown’s high-pitched voice — a little Bon Scott, a little Geddy Lee — walks an androgynous line as he introduces listeners to the dreamy Noelle, whose “boyfriend’s a d--k.” The heartsick teen gets the girl in this one, thanks to a shared appreciation of Iron Maiden. The song may have appeared on the Dawson’s Creek soundtrack back in 2000, but it was way more in tune with the far superior Freaks and Geeks. -- C.W.

28. Faith Hill, "The Way You Love Me" (No. 6, Hot 100)

One of the tunes blaring most often around today’s industry is about the lack of female artists on country radio -- but that wasn’t the case 20 years ago when fans were treated to Reba McEntire, Martina McBride, Shania Twain, and this ditty by Faith Hill. Between a head-bobbin’ track fusing elements of country, pop and dance, colorful lyrics (“If I could grant you one wish / I'd wish you could see the way you kiss …”) and Hill’s exuberant vocals, the song perfectly captures the euphoria that comes with love. -- G.M.

27. 3 Doors Down, "Kryptonite" (No. 3, Hot 100)

The Kinks wished they could fly like Superman; Our Lady Peace pronounced him dead. As the post-grunge boom extended into the new millennium, an unknown band from the swamps of Mississippi swooped into rock 'n' roll's Man of Steel canon and eclipsed the competition. "Kryptonite" was omnipresent on rock and pop radio, broadcasting 3 Doors Down vocalist Brad Arnold's everyman musings on superhuman strength, and frequent lack thereof. -- C.P.

26. Dr. Dre feat. Eminem, "Forgot About Dre" (No. 25, Hot 100)

Just in case you forgot about Dre during the seven years between his solo debut and his sophomore effort, the Aftermath founder and protege Eminem reminded critics of his impact with this Grammy-winning hit off 2001. “Still the same O.G./ But I been low-key,” the N.W.A rapper admits before launching into his accomplishments. “Who you think brought you the oldies/ Eazy-Es, Ice Cubes, and D.O.Cs/ The Snoop D-O-double-Gs/ And the group that said motherf--k the police.” Em’s alter ego Slim Shady also makes a memorable appearance to wreak havoc and defend the rapper’s legacy against critics. -- A.C.

25. Ludacris feat. Shawnna, "What's Your Fantasy" (No. 21, Hot 100)

One of the biggest rap stars of the '00s jumped out with a breakthrough hit where every salacious lyric was designed to hold your attention -- a career's worth of punchlines, it seemed, until we realized that all of his singles were kinda like that. Three years before Lil Jon & the Eastside Boyz took us from the window to the wall, their fellow ATLien went everywhere from the 50-yard-line of the Georgia Dome to the White House, lick-lick-lick-licking any competition for the honors of being the most verbally creative or dextrous new MC of the early 21st century. -- A.U.

24. Destiny's Child, "Jumpin' Jumpin'" (No. 3, Hot 100)

Destiny’s Child all but invented the club on “Jumpin’,” the contagious soundtrack to a girls’ night out that gifted us one of the early decade’s most memorable choruses. Beyoncé co-produced the upbeat track, which was the final single off the group’s album The Writing's on the Wall, laying the groundwork for her own solo sound and sing-rap cadence -- and her power. To this day, if Bey says the party starts at “11:30,” you better arrive on the dot. -- T.C.

23. Moby, "Porcelain" (No. 18, Hot 100)

Moby crafted profound and paradigm-shifting music that seemed to be a perfect prediction of what the millennium might sound like, and it’s only fitting that “Porcelain” from his 1999 electronica opus Play didn’t quite catch on until the turn of the century. With its enveloping reversed strings loop, divine piano melody and spiritual calls from the ether, “Porcelain” created an eye-opening experience that pushed the music world into the endless possibilities of converging genres. Though he’d attain an atypical celebrity status that would ultimately turn him into a punchline within two years, the peak of Moby’s phenomenon in “Porcelain” will endure forever. -- B. Kress

22. Blink-182, "Adam's Song" (No. 2, Alternative Songs)

“Adam’s Song,” though not the first of its kind by any stretch, directly grapples with mental health in a way that likely makes the powerful song more suited for today’s era of alternative music over its turn-of-the-millennium origin. It’s not that heavy topics such as suicide, depression and anxiety have become a more prevalent part of the human experience since the song’s release; rather, the discussion surrounding them has thankfully become far less taboo. The slower, more considered "Adam's Song" was both a sonic and thematic departure from the Blink-182 norm -- “What’s My Age Again” and “All the Small Things” served as the other two singles on Enema of the State -- but lyrics like “please tell mom this is not her fault” still serve as some of the band’s most poignant. -- J.G.

21. Sisqo, "The Thong Song" (No. 3, Hot 100)

If you think about it, the "Thong Song" went against everything conventional. For starters, Sisqo was singing about thongs -- with a passion usually reserved in R&B for love and vengeance. Then, he repeats the same verse three times. And third, he hopscotches his way through those verses with Ricky Martin references and cheesy one-liners like "she got dumps like a truck." In 2020, the "Thong Song" might not make sense, but in 2000, this booty-shaking record caused enough tremors to land at No. 3 on the Billboard Hot 100. -- C.L.

20. Eminem, "The Real Slim Shady" (No. 4, Hot 100)

As he's done from the start of his career until, well, basically his most recent album dropped in January, Eminem takes aim at his perceived adversaries in this masterfully manic Marshall Mathers LP lead single. He paints a lyrical bull's-eye on everyone from (the now-very-outdated) Tom Green to the "little girl and boy groups" peppered throughout this very list. But as much as Em's bars mock the world of pop with cutting precision, this song and its VMAs-dominating video cemented Slim Shady's place in that very universe, skyrocketing him to the top five of the Hot 100 for the first time. -- K.A.

19. Madonna, "Music" (No. 1, Hot 100)

The deck has always been stacked against women in pop the further they climb into adulthood, so if Madonna was gonna top the Hot 100 for four consecutive weeks at age 41, she would need a surefire radio winner with cross-generational appeal. Enter her Mirwais collab "Music," a dancefloor call-to-arms boasting a faint patina of electroclash for the club kids, a throbbing techno beat for suburban ravers and enough old-school electro-funk that her middle-aged fans could still nod along -- Madge making the people come together for the third straight decade. -- J. Lynch

18. *NSYNC, "It's Gonna Be Me" (No. 1, Hot 100)

The second single from *NSYNC's No Strings Attached, "It's Gonna Be Me" further ushered in the group's era of attitude. A Max Martin co-penned classic -- though production was handled solo by his oft-overlooked collaborator Rami Yacoub -- the track encourages realizing your worth and refusing to get pushed aside. When it comes to pop culture, it's the epitome of a song that endures: As long as millennials are around, there won’t come an April 30th when Justin Timberlake is not plastered across the internet singing “It’s gonna be MAY.” If meme clout isn’t enough for you, put some respect on its name anyway: "It's Gonna Be Me" was the only *NSYNC song to ever hit No. 1 on the Hot 100. -- B. Kaminsky

17. Papa Roach, "Last Resort" (No. 57, Hot 100)

Suicide has been a subject in popular music for decades, but there’s never been a song, before or since, quite like Papa Roach’s “Last Resort,” an absolutely pummeling pop-metal track performed from a place of total anguish. From the cold open (“Cut my life into pieces / this is my last resort!”) to the breakdown in which singer Jacoby Shaddix breaks down in sob-shrieks (“I! CAN'T! GO! ON! LIV! ING! THIS! WAY!”), “Last Resort” leans into the urgency of such a traumatic situation -- any breaks in singing are filled with zigzagging guitars or bashed drums -- and never stops shaking its listener awake. With such personal pain being communicated openly and honestly, “Last Resort” has persisted as a profoundly cathartic take on a dark subject, and as arguably the finest single of the nu-metal era. -- J. Lipshutz

16. Christina Aguilera, "What a Girl Wants" (No. 1, Hot 100)

First recorded by French singer Ophélie Winter, "What a Girl Wants" found Christina Aguilera taking a glitchy, R&B-tinged pop single -- expressing gratitude for a genuinely patient and empathetic boyfriend -- and translating it into her second consecutive Hot 100 chart-topper with the ease of a rising global superstar. Twenty years after its release, "What a Girl Wants" can still take any child of the late 1990s back to summers filled with choppy haircuts and bare midriffs. -- T.M.

15. Dixie Chicks, "Goodbye Earl" (No. 19, Hot 100)

After the Dixie Chicks earned their fourth country No. 1 with the lovestruck ballad “Cowboy Take Me Away,” the trio loudly reminded the world of their audacity with “Goodbye Earl.” Over a banjo-tinged stomp, frontwoman Natalie Maines graphically narrates an abusive marriage (“She'd put on dark glasses or long sleeved blouses/ Or make-up to cover a bruise"), but by the time the first chorus hits, the song becomes a tale of vengeance -- oh, and murder. While the Dixie Chicks have proven their fearlessness throughout their decades-spanning career, “Goodbye Earl” is arguably the Chicks’ boldest display to date, both thanks to its black-comedy lyrics and Maines’ fiery delivery -- which, not for nothing, makes it still one hell of a karaoke crowd-pleaser decades later. -- T.W.

14. Aaliyah, "Try Again" (No. 1, Hot 100)

First impressions aren't everything: That's the message behind "Try Again," a slinky, Timbaland-produced jam from the Romeo Must Die soundtrack, which sees Aaliyah telling her potential paramour not to give up on her if she seems shy at first. Just as a baby's cries whimsically soundtracked the late star's "Are You That Somebody?," Tim's omnipresent "wiki-wiki"s in "Try Again" put the producer's singular stamp front and center. It's a potent pop pairing, which resulted here in the first Hot 100 No. 1 for either -- and was cut short far too soon by Aaliyah's untimely death at age 22 just a year later. -- K.A.

13. Red Hot Chili Peppers, "Californication" (No. 69, Hot 100)

It’s deliciously ironic that Californication, the Red Hot Chili Peppers’ meditation on Hollywood’s dark underbelly, was also one of their biggest commercial successes. Should we be worried that it holds up so well? The beloved title track is a tumble of omens that read like riddles (“psychic spies from China;” “silver screen quotation”), with references to porn, plastic surgery, Kurt Cobain and Star Wars, sung over ominous guitar strums courtesy of John Frusciante, who had just resumed duties as the band’s guitarist. Along with its classic fake-video game video, "Californication" helped make RHCP as big as ever at the start of the 2000s -- and if nothing else, its sheer number of “-ation” rhymes is worthy of a medal. -- T.C.

12. Dr. Dre feat. Snoop Dogg, "The Next Episode" (No. 23, Hot 100)

In 1999, Dr. Dre and Snoop Dogg followed up their landmark “Nuthin' but a 'G' Thang” with a sequel for a new age. With those opening horns, borrowed from David Axelrod and David McCallum’s “The Edge,” Dre and his one-time mentee stepped out of the lowrider and into something newly slick, developing a West Coast sound that looked out at the future while still managing to respect its roots. The result was as inspired as “‘G’ Thang,” and timeless -- the next step for Snoop and Dre, after their brief spat, and for the style they’d already revivified. -- W.G.

11. Jay-Z feat. UGK, "Big Pimpin'" (No. 18, Hot 100)

There was once a time when Jay-Z was a brash Brooklyn playboy, who relished living life on the edge -- a rap version of Jordan Belfort. "Big Pimpin'" encapsulates that era of Jigga and his braggadocious ways. Not only does he refuse to wave the white flag on any budding romances ("I'll be forever mackin'"), but he also brags about his long-lasting stamina when going head-to-head with TV bombshells like Pamela Anderson. Throw in a Timbaland beat as big as a luxury liner, a timeless Bun B hook, and Pimp C's squeaky clean verse about his player ways, and you've got yourself an MTV Jam of the Week for all time. -- C.L.

10. Nelly, "Hot (S***) Country Grammar" (No. 7, Hot 100)

The Midwest had already gifted the world Eminem via Detroit, but when Nelly's debut LP Country Grammar dropped on June 27, 2000, the world got a vastly more celebratory injection of middle American hip-hop, courtesy of the St. Louis rapper. The album's title track and lead single was an homage to the come up, going "from broke to having brokers" and "down-down-baby your street in a Range Rover," as Nelly flossed in the classic sing-along chorus. Built on a hypnotically effervescent beat from producer Jay E -- a St. Lunatics affiliate credited with developing the St. Louis sound -- "(Hot S**t) Country Grammar" hit the Hot 100's top 10, and was the song of the summer for kids from St. Louis to Memphis, from Texas back up to Indiana and beyond. -- K.B.

9. Macy Gray, "I Try" (No. 5, Hot 100)

If you went through a break-up circa 2000, odds are, Macy Gray helped you weather it. The raspy-voiced soul singer’s best-known single is a loping anthem about coming to terms with your emotions with a cathartic, instant-classic chorus that falls somewhere between heartbreaking and freeing. It feels like a good cry -- and came with an equally tear-jerking music video. The song was nominated for record and song of the year at the 2001 Grammys, where it also picked up best female pop vocal performance, and spent 27 weeks on the Hot 100, peaking at No. 5. Gray released a new, jazz-infused version in 2016, but it’s the poignant original that gets us every time. -- T.C.

8. DMX, "Party Up (Up in Here)" (No. 27, Hot 100)

Going off like the alarm clock to wake up all of post-Y2K America, "Party Up (Up in Here)" was a truly singular ode to going buckwild from a man who knew of what he f--king spoke. Over a Swizz Beatz production that screeches at you to cut the red wire, DMX lets it rip like Randy Johnson coming in for one inning of bullpen work, sounding all the scarier because the chorus implies he hasn't even truly lost his mind or his cool yet. And despite directly threatening murder in the song's first and third verses, it's the second verse where X truly comes off cold-blooded, running down a gut-busting checklist of reasons the competition can't compare: "You're wack, you're twisted, your girl's a ho/ You're broke, the kid ain't yours, and everybody know..." Preacher tellin' the truth, and it hurts so good. -- A.U.

7. Jennifer Lopez, "Love Don't Cost a Thing" (No. 3, Hot 100)

J.Lo’s smash hit “Love Don’t Cost a Thing,” which peaked at No. 3 on Billboard’s Hot 100, became an instant staple in her catalogue. The break-up anthem, which she included in her epic Super Bowl Halftime Show this February, has stood the test of time because of its catchy, hip-hop-tinged beat, and because of Lopez keeping it real with lyrics about her need for true love without a price tag (“All that matters is that you treat me right”). A memorable dance routine in the song's music video helped, with millions watching trying to get those dance moves down to hopefully one day show them off on the dancefloor. -- G.F.

6. D'Angelo, "Untitled (How Does It Feel)" (No. 25, Hot 100)

The video for “Untitled” provoked a collective swoon heard around the country -- thanks to D’Angelo’s lean, muscled torso and teasing camera shots that lingered near the singer-songwriter’s equally chiseled nether region. But video aside, the song was a game-changer that solidified D’Angelo’s status as one of R&B's most innovative talents. The slow grind of the song’s sultry, sensuous track took lovemaking music to the next level, following earlier connoisseurs such as Marvin Gaye and Prince. And while men had usually dominated romantic propositions in song to that point, D’Angelo gave females an equal role in “Untitled.” As the first verse lays out: “Have it your way/ And if you want you can decide/ That if you'll have me/ I can provide everything that you desire.” Winning a Grammy for best male R&B vocal performance, D’Angelo delivered one of the last great hurrahs in the genre's neo-soul movement. -- G.M.

5. OutKast, "B.O.B. (Bombs Over Baghdad)" (No. 69, R&B/Hip-Hop Songs)

Can a song be massively influential even if nothing that comes after really sounds like it? "B.O.B." is the OutKast legacy, packed into five manic minutes. Andre 3000 and Big Boi trade indomitable verses, but all hip-hop convention ends there: Gospel and glam rock battle for air space, time and tempo escalate to oblivion, and a choir-sung chorus eerily preludes the new world order lurking over 2000's shoulder. In reality, OutKast wrote the Stankonia single more concerned with American ghettos than any foreign policy; Andre used "bombs over Baghdad" as a sonic non sequitur, pulled from an overheard news broadcast. "B.O.B." can signify almost everything, next to nothing, or just rap's greatest duo innovating at maximum capacity. -- C.P.

4. Eminem feat. Dido, "Stan" (No. 51, Hot 100)

Eminem has (correctly) been lambasted for his fealty to the actually f--ked-up f-word, but credit where credit's due -- at the turn of the century, no major rapper was going out of their way to convey matter-of-fact empathy for a jilted, pathological fan seeking a same-sex romantic connection. Over an insistent whisper of a beat and that haunting rework of Dido's "Thank You," Marshall Mathers paints a brutally vivid portrait of celebrity fixation as a distraction for economic and emotional poverty. Horrorcore is often more human than horror at its core, and the unsparing conclusion to "Stan" still pains the soul two decades later – so much, in fact, that society had to reimagine the title character in terms of 'net slang in order to smirk through the unwanted feels. -- J. Lynch

3. Britney Spears, "Oops!...I Did It Again" (No. 9, Hot 100)

How can you avoid a sophomore slump? Easy: Just reassemble the team who worked on your debut smash, squeeze on a red latex catsuit and shoot a video that’s truly out of this world. Britney Spears followed this recipe for success with "Oops!...I Did It Again,” her “not that innocent” lead single from the album of the same name. Spears once again linked with Max Martin and Rami Yacoub, the duo behind “...Baby One More Time,” for a whomping pop smash about toying with someone’s emotions. The playfulness turns straight-up goofy with a spoken-word bridge that references the diamond necklace from Titanic, not to mention a video set in Spears’ space lair on Mars and a romance with an astronaut. Though “Oops!” didn’t reach the same chart heights as “...Baby,” peaking at No. 9 on the Hot 100, it’s fair to say that with this single, yes, she did it again. -- C.W.

2. *NSYNC, "Bye Bye Bye" (No. 4, Hot 100)

There's no better way to say hello to a brand-new era than by saying "bye bye bye" to the past. This super-powered pop smash was the first single from *NSYNC's landmark sophomore album No Strings Attached, on which the blockbuster boy band very publicly cut ties with their unscrupulous creator, late music and blimp impresario Lou Pearlman, to finally get their fair share of the pop pie. Of course, it's tough to make a fun hit song out of shady business dealings with your boss, so the lyrics instead address a toxic romantic relationship -- though lines like "life would be much better once you're gone" and "I don't want to be the loser and I've had enough" could easily go both ways.

The thing that endures about the song is that repetitive earworm of a chorus -- "It ain't no lie/ Baby, bye, bye, bye" -- and its accompanying triple-hop dance, made famous in the quintet's iconic big-budget music video. You might be surprised to learn that "Bye Bye Bye" topped out at No. 4 on the Hot 100, but the video -- with its metaphorical marionette-puppet choreography -- dominated the No. 1 spot on MTV's Total Request Live for 25 consecutive days. No Strings Attached went on to sell 2.4 million copies in its first week -- a record-setting achievement that lasted 15 years, until Adele's 25 came along -- and it all started with this undeniable lead single. -- K.A.

1. Destiny's Child, "Say My Name" (No. 1, Hot 100)

What did late-‘90s/early-‘00s R&B artists do when they were heartbroken? Most ran to their nearest piano to pen a gutwrenching ballad. Some waited for the next torrential downpour to sing their poor hearts out. But Destiny’s Child, one of the genre’s most rule-breaking girl groups, took an alternative approach: After building a career on female empowerment and kiss-off anthems -- “No, No, No Pt. 2,” “Bills, Bills, Bills," “Bug a Boo” -- the foursome tweaked their formula, with an approach that focused on the paranoia underlining their unstable relationships.

Say my name. Say my NAME. SAY MY NAME! Ladies, we’ve all been there before: The more you utter that single phrase, it becomes harder to suppress the irritation that bubbles with each sharp syllable. That kind of indignation doesn’t call for pretty piano melodies or sprawling vocal runs, oh no. With Rodney Jerkins’ 808-heavy production, each syncopation heightened the members’ flawless harmonies and Beyoncé’s innovative staccato, rap-inspired flow. You can almost hear her trying to contain her emotions as the anxious lyrics barely escape gritted teeth: “Every other word is ‘uh-huh, yeah okay’/ Could it be that you are at the crib with another lady?” The song was even grounded in the reality of its lead songwriter, the late LaShawn McDaniels, who found his girlfriend would snap with suspicion at him whenever she heard voices in the background of his phone calls: "She'd be like, 'Well, say my name then, and tell me that you love me,'" he told the Recording Academy in 2019.

Sure, “Say My Name” has been branded somewhat by the real-world messiness its release encompassed: the accompanying video infamously announced the group’s new line-up, replacing LeToya Luckett and LaTavia Roberson with Michelle Williams and Farrah Franklin. But despite the background drama, the single went on to win two Grammys, top the Hot 100 and create an everlasting legacy that lives through a Coachella reunion, an onslaught of covers and interpolations, and -- most recently -- a chilling horror remake. Even after two decades, the song’s universal relatability still hasn’t let up. As long as there are triflin', good for nothing type of brothas around, women will be at the ready to question their sudden change. -- B.G.