Entering the year 2000, there was a palpable sense of anticipation for a new sound, something groundbreaking to match the dawn of a new millennium. While the complete sonic revolution some might have expected didn’t entirely materialize overnight, the music of 2000 did represent a significant evolution, building upon the foundations laid in the late 90s while confidently striding into the future.
The turn of the millennium didn’t erase the artists who dominated the charts at the close of the 20th century. In fact, many of the biggest names of 1999 – the ubiquitous boy bands and powerful girl groups, the chart-topping rappers, and the rock titans – remained at the forefront in 2000. However, there was a distinct sense of reinvigoration, a collective push to elevate their sound and musical landscapes to reflect this pivotal moment in time. This wasn’t just a continuation; it was a calculated step forward.
Fueling this musical metamorphosis were some of the most innovative and influential producers of the era. Timbaland and Rodney “Darkchild” Jerkins, masters of sonic architecture, intensified the drama and emotional depth within R&B, crafting tracks that felt like they belonged in a futuristic opera house. The Neptunes and Swizz Beatz, sonic architects in their own right, injected hip-hop with an arsenal of cutting-edge sounds, from literal bells and whistles to groundbreaking synth textures, paving the way for the genre’s ascent to mainstream dominance. And, of course, Max Martin, the architect of TRL pop, continued to refine and mature his signature sound, proving that pop music and its leading figures were not relics of the 90s, destined to be left behind with Trapper Keepers and Tamagotchis.
The 100 Greatest Songs of 2000
But 2000 wasn’t solely about established 90s stars simply upgrading their formulas. The hip-hop landscape experienced a seismic shift with the emergence of a new rap icon hailing from the heartland of America, challenging the coastal dominance traditionally associated with the genre. R&B underwent a parallel modernization, expanding beyond its poppiest iterations to embrace its deeper roots, with the burgeoning neo-soul movement enjoying a year of unprecedented commercial and critical acclaim. Even artists who rose to fame in the 80s returned with dramatically transformed sounds, demonstrating their enduring relevance and adaptability as they entered their third decade in the music industry.
As *NSYNC’s No Strings Attached, a landmark 2000 pop album renowned for its cutting-edge production and record-shattering commercial success, reached its 20th anniversary, and with many seeking refuge and nostalgia in 2020, payoffsong.com decided to dedicate a week to celebrating the year 2000. We begin this journey with a curated list of our 100 favorite songs from this historically rich year, and throughout the week, we will present a series of articles, interviews, lists, and reflections that delve deeper into the beginning of the new millennium. Join us as we explore the sounds that defined the year 2000 and revisit the songs that continue to resonate today.
Before we dive into the countdown, let’s clarify our selection criteria: Songs were considered eligible for this list if they were released as singles in 2000, debuted on the Billboard charts in 2000, or reached the No. 1 position in 2000. However, to maintain focus on the year 2000, songs that didn’t break into the Hot 100 until 2001, or debuted in 2000 but didn’t reach No. 1 until the following year, will be considered for our 2001 list. So, while tracks like “Ms. Jackson,” “It Wasn’t Me,” “Yellow,” “One Step Closer,” and “One More Time” are iconic, we’ll likely see them on next year’s retrospective.
Explore our list of the Top Songs 2000 below, find a Spotify playlist featuring all 100 tracks at the end, and revisit payoffsong.com throughout the week for more in-depth stories behind the most captivating songs and albums of the year 2000. It’s time to take a nostalgic trip back to the start of the millennium with 100 incredible songs that defined a generation.
100. Zombie Nation, “Kernkraft 400” (Sport Chant Stadium Remix) (No. 99, Hot 100)
The late 90s witnessed an interesting convergence between video game music and sports anthems, blurring the lines between digital entertainment and live sporting events. “Kernkraft 400” perfectly encapsulates this phenomenon. This high-energy dance track, a remix of a video game theme, layered with a soccer chant, became the ultimate mind-numbing anthem as the millennium turned. Think of it as “Seven-Bit Nation Army,” delivering pure, unadulterated energy without the distraction of verses. It was a sound perfectly crafted for both the dance floor and the stadium. — ANDREW UNTERBERGER
99. P!nk, “There You Go” (No. 7, Hot 100)
Before P!nk became synonymous with acrobatic performances and stadium-sized pop anthems, she was introduced to the world as a promising R&B artist with her breakout single, “There You Go.” The track’s swaggering production and soulful vocal delivery led many to initially believe that P!nk was a light-skinned Black artist, highlighting the song’s authentic R&B feel. While this wasn’t the case, “There You Go” firmly established P!nk as an artist who would defy genre conventions and resist being pigeonholed into the bubblegum-pop mold that dominated the Y2K era. — BIANCA GRACIE
98. O-Town, “Liquid Dreams” (No. 10, Hot 100)
For a snapshot of who and what was culturally relevant in 2000, look no further than O-Town’s “Liquid Dreams.” This track is a time capsule of early millennium pop culture, name-dropping icons like Destiny’s Child, Madonna, Janet Jackson, Angelina Jolie, Cindy Crawford, Tyra Banks, and Salma Hayek. The infectious beat and catchy melody made it a dynamic debut for O-Town, the first group to emerge from Diddy’s Making the Band reality series, propelling it into the Hot 100 top 10. Perhaps the most ingenious aspect of “Liquid Dreams” is its sheer catchiness, so effective that listeners might overlook the fact that it’s essentially a song about a wet dream. — TAYLOR WEATHERBY
Image alt text: O-Town performing “Liquid Dreams” music video, showcasing early 2000s boy band pop culture.
97. The White Stripes, “Hello Operator” (Did not chart)
In a year where rock music was heavily influenced by “nu” metal bands like Limp Bizkit and Linkin Park, The White Stripes offered a refreshing throwback with their raw, blues-infused garage rock sound. From their sophomore album De Stijl, the Detroit duo’s “Hello Operator” stands out as a raucous and righteously dirty track. Jack White’s guitar work is scorching, while Meg White’s minimalist drums provide a skeletal yet powerful backbone to this headbanging anthem. In just 2 minutes and 36 seconds, “Hello Operator” proved that authentic 20th-century rock was not only alive but thriving in the new millennium. — KATIE BAIN
96. Toby Keith, “How Do You Like Me Now?!” (No. 31, Hot 100)
Seven years after his breakthrough hit “Should’ve Been a Cowboy,” Toby Keith revitalized his career after a period of less successful singles with “How Do You Like Me Now?!” This honky-tonk anthem is a playful send-off to the high school “it-girl” who once dismissed him. While high school Toby’s tactics might be questionable – breaking into the stadium to write her number on the 50-yard line – the song’s hooks are undeniably strong. The chorus is an absolute knockout, soaring through the airwaves and reclaiming Toby Keith’s position in country music. — CHRIS PAYNE
95. Mandy Moore, “I Wanna Be With You” (No. 24, Hot 100)
Mandy Moore was only 16 when she released “I Wanna Be With You,” which became her biggest Hot 100 hit. This wispy ballad of teenage longing shares similarities with Jessica Simpson’s “I Wanna Love You Forever,” but possesses a tenderness and yearning that hinted at Moore’s future singer-songwriter direction. “I Wanna Be With You,” with its soft-hearted lustfulness and sighing vocals, can be seen as a TRL-era update to the Beach Boys’ classic “Wouldn’t It Be Nice.” — A.U.
94. Black Rob, “Whoa!” (No. 43, Hot 100)
While The Notorious B.I.G. and Ma$e were Bad Boy Records’ flagship artists in the 90s, Diddy solidified his roster by signing Harlem lyricist Black Rob in 1997. In 2000, Black Rob delivered a powerful return with his war-ready single “Whoa!” Packed with grit and New York swagger, “Whoa!” is a quintessential East Coast banger, showcasing raw energy and lyrical flexing at its finest. — CARL LAMARRE
93. The Dandy Warhols, “Bohemian Like You” (No. 28, Alternative Songs)
There’s a layer of self-awareness in The Dandy Warhols crafting a highly popular and memorable song about the contradictions of hipster culture. “Bohemian Like You,” featured in commercials and becoming their biggest hit, sharply satirizes the pseudo-counter-culturalism that began to define the late 90s and early 2000s. This track made indie-rock stars out of The Dandy Warhols, thanks to its catchy critique of alternative pretension. — STEPHEN DAW
92. Miss Kittin & The Hacker, “Frank Sinatra” (Did not chart)
With the cool detachment of Marlene Dietrich, French electroclash pioneer Miss Kittin delivers “Frank Sinatra,” recounting the scandalous nightlife of the Rat Pack icon over a minimalist, icy beat. The song’s blunt humor and brazen delivery have ensured its cult status. While electroclash’s mainstream moment was fleeting, “Frank Sinatra’s” fetishized blend of synth-pop and 90s house music foreshadowed trends that continue to influence dance music today. — JOE LYNCH
91. Hanson, “This Time Around” (No. 20, Hot 100)
Marketed as Hanson’s “We’re adults now!” single, “This Time Around,” the title track from their 2000 album, faced the daunting task of following up their massive 1997 debut, Middle of Nowhere, and proving that the “MMMBop” kids could mature musically. While not a chart-topping smash, “This Time Around” is a solid pop-rock track, featuring a memorable piano line and sing-along chorus that hinted at Hanson’s future as respected adult songwriters, even if they never fully returned to their initial radio pop heights. — JASON LIPSHUTZ
Image alt text: Hanson brothers performing “This Time Around” music video, showcasing their evolution from teen pop to pop-rock.
90. PJ Harvey, “Good Fortune” (Did not chart)
“Good Fortune” marked a significant shift for PJ Harvey. The lead single from Stories from the City, Stories from the Sea features a quicker tempo, romantic lyrics, and an immediately catchy melody, differentiating itself from the darker tones of Is This Desire? and the complex arrangements of To Bring You My Love. “Good Fortune” predates Liz Phair’s 2003 crossover hit “Why Can’t I?” yet achieves a balance that is uniquely PJ Harvey – still too distinctive for mainstream radio programmers, but undeniably captivating. — ERIC FRANKENBERG
89. 2Gether, “The Hardest Part About Breaking Up (Is Getting Back Your Stuff)” (No. 87, Hot 100)
“The Hardest Part About Breaking Up (Is Getting Back Your Stuff)” is a pitch-perfect parody of TRL boy band jams. Complete with fake fans raving in the video’s corner, this track nails the boy band breakup song formula so effectively that you might expect Max Martin and Rami Yacoub to be credited. (Co-writers Brian Kierulf and Joshua M. Schwartz did go on to work on Britney Spears’ Britney album.) While the lyrics are humorous and relatable, the true highlights are the ad-libs, like the strangled “meow!” following the chorus line “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 became synonymous with tear-jerking ASPCA commercials featuring “Angel,” she was known for her emotionally resonant vocals as a solo artist and as a guest vocalist for the new age/electronic project Delerium. “Silence,” a collaboration between McLachlan and Front Line Assembly’s Bill Leeb and Rhys Fulber, reached new heights by combining McLachlan’s ethereal vocals with Gregorian chants and a driving beat. “Silence” has endured through club remixes, most notably Tiesto’s epic In Search of Sunrise edit, and its dark, ethereal influence can still be heard in contemporary artists like Grimes. — ANNA CHAN
87. Hoku, “Another Dumb Blonde” (No. 27, Hot 100)
At a time when female pop stars were employing suggestive schoolgirl outfits and genie metaphors to attract attention, Hawaiian artist Hoku, at just 18, offered a refreshing alternative with her debut single, “Another Dumb Blonde.” This track is a spirited “get lost” anthem directed at shallow players. “Another Dumb Blonde” is feisty from beginning to end, calling out a superficial jerk for his lack of genuine interest (“Lately I’ve come to find/ That you’re not really interested in my heart or mind”). The song transformed the “dumb blonde” stereotype into an empowering anthem for heartbroken teens, regardless of 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 become a beloved wedding anthem. Jagged Edge’s enduring ballad checks all the boxes of classic R&B: silky harmonies, smooth rhythms, and heartfelt lyrics about true love and commitment. Reaching No. 1 on the Hot R&B/Hip-Hop Songs chart and No. 11 on the Hot 100, “Let’s Get Married” was further boosted by a popular Run-D.M.C.-sampling remix featuring Reverend Run. In an era increasingly dominated by songs focused solely on fleeting physical intimacy, “Let’s Get Married” reminds us of the enduring appeal of songs about lasting romantic commitment. — GAIL MITCHELL
Image alt text: Jagged Edge performing “Let’s Get Married” music video, capturing the essence of 2000s R&B romance.
85. Ricky Martin, “She Bangs” (No. 12, Hot 100)
By the time “She Bangs” was released as the lead single from his second English-language album, Sound Loaded, in October 2000, Ricky Martin was already a certified hitmaker. With seven Hot 100 hits under his belt, “She Bangs” further solidified his status. This danceable track seamlessly blended salsa flair with rock guitar and an irresistible pop beat, achieving universal appeal and reaching the top 20 on the Hot 100 and the top five in eight countries outside the U.S. However, “She Bangs” might be most memorably associated with William Hung’s infamous American Idol audition. — TAYLOR MIMS
84. Beenie Man feat. Mya, “Girls Dem Sugar” (No. 54, Hot 100)
Beenie Man had already achieved US breakthrough success with the rugged dancehall crossover “Who Am I (Sim Simma)” in 1998. As he became more established stateside, he expanded his sonic palette, collaborating with The Neptunes for “Girls Dem Sugar.” The Neptunes reimagined elements of “Who Am I,” transforming the original into a glossy, scratch-heavy club anthem, elevated by Mýa’s dreamy vocals. This collaboration showcased the evolving sound of dancehall in the early 2000s. — B.G.
83. Carlos Vives, “Fruta Fresca” (No. 1, Latin Songs)
“Fruta Fresca,” the lead single from Carlos Vives’ El Amor de Mi Tierra (1999), shook Latin music traditionalists as it topped the Latin Songs chart in the early 2000s. Produced by Emilio Estefan and Juan Vicente Zambrano, this track blended swirling vallenato rhythms with pop sensibilities, revolutionizing Latin music without compromising Vives’ artistic integrity. “Fruta Fresca” opened with enigmatic electro-acoustic guitar chords, transitioning into Vives’ energetic vocals, supported by robust bass and percussion. Vives skillfully fused Colombian folk music with Latin pop, becoming a leading figure in the mainstream tropical music scene. — PAMELA BUSTIOS
82. Limp Bizkit, “Break Stuff” (No. 14, Alternative Songs)
For anyone who experienced the nu-metal explosion of the early 2000s, the opening chunky two-chord riff of Limp Bizkit’s “Break Stuff” is instantly recognizable and rage-inducing. This single from Significant Other was tailor-made for mosh pits, culminating in Fred Durst’s primal scream, “Give me something to break!” “Break Stuff” captures a relic of the era at its most exaggerated, dumb, and undeniably impactful. — J. Lipshutz
81. Carl Thomas, “I Wish” (No. 20, Hot 100)
Many great R&B torch songs explore unrequited love, but Carl Thomas’ “I Wish” stands out for lamenting a love that was requited, yet ultimately unattainable: “I love her so, she’s got love for me/ But she still belongs to someone else.” This unique heartbreak ballad avoids sentimentality thanks to Mike City’s breezy, piano-led production and Carl Thomas’s soaring vocal performance. Despite its quality, “I Wish” became a popular source for off-key imitations, including Jay-Z’s interpolation. — A.U.
Image alt text: Carl Thomas performing “I Wish” music video, emphasizing the emotional depth of 2000s R&B.
80. 3LW, “No More (Baby I’ma Do Right)” (No. 23, Hot 100)
3LW, the trio of “3 Little Women,” addressed common relationship problems with their hit “No More (Baby I’ma Do Right).” Dealing with a cheating boyfriend and his suspicious pager activity, the group – with the youngest member only 14 – declared they wouldn’t tolerate it any longer. This catchy kiss-off anthem resonated with young audiences facing similar relationship frustrations in the early 2000s. — KATIE ATKINSON
79. Sting feat. Cheb Mami, “Desert Rose” (No. 17, Hot 100)
Fifteen years into his successful solo career post-Police, Sting enjoyed the artistic freedom to pursue diverse musical directions. “Desert Rose,” with its global influences, reflects this. With the grandeur of a Disney musical and the ethereal ambiance of Pure Moods compilations, “Desert Rose” transported listeners to an enchanted sonic oasis. The song’s music video, featuring Sting driving a 2001 Jaguar S-Type to meet Algerian singer Cheb Mami, further cemented its exotic and slightly over-the-top appeal. — C.P.
78. Kylie Minogue, “Spinning Around” (Did not chart)
While some artists aimed for radical innovation at the millennium, Kylie Minogue opted for a different approach. “Spinning Around” embraced a classic, disco-inspired Europop sound that defined her 21st-century career. This track achieved massive success globally, though initially less so in the US. “Spinning Around’s” danceable melodies and irresistible beat proved that sometimes, sticking to timeless formulas while adding a modern twist can be just as effective as reinvention. — S.D.
77. Samantha Mumba, “Gotta Tell You” (No. 4, Hot 100)
Samantha Mumba’s debut album, Gotta Tell You, remains a somewhat underappreciated gem of early 2000s bubblegum pop. The title track, her debut single, showcases a soulful confidence that belied Mumba’s young age of 17. With a powerful minor-key chorus, “Gotta Tell You” is a standout pop banger. The music video, featuring Mumba’s impressive front flip off a store awning, further cemented its memorable status. — KEVIN RUTHERFORD
76. The Baha Men, “Who Let the Dogs Out?” (No. 40, Hot 100)
“Who Let the Dogs Out?” is one of those enduring cultural questions, alongside “chicken or the egg?” and “how many licks to the center of a Tootsie Pop?” While the culprit remains unknown two decades later, The Baha Men’s Grammy-winning stadium anthem remains an inescapable party starter. Queue it up, embrace the silliness, and join in with a “yippie, yi, yo!” or two. — JOSH GLICKSMAN
Image alt text: The Baha Men performing “Who Let the Dogs Out” music video, capturing the infectious energy of the Grammy-winning stadium anthem.
75. Erykah Badu, “Bag Lady” (No. 6, Hot 100)
Erykah Badu’s soulful classic “Bag Lady” is essentially a mini-therapy session set to music. With its soothing beat and timeless wisdom (“All you must hold onto is you”), the song offers guidance on letting go of emotional baggage. A sample from Dr. Dre’s “Xxplosive” adds a subtle flourish to the minimalist sound. “Bag Lady,” nominated for two Grammys and peaking at No. 6 on the Hot 100, remains Badu’s highest-charting single to date. — TATIANA CIRISANO
74. Air, “Playground Love” (No. 28, Dance Singles Sales)
Air’s “Playground Love,” though released in 2000, possesses a timeless quality that evokes the 1970s. With dream-pop melodies and soothing vocals, the song captures a sense of hopeless romanticism. Featured on the soundtrack to Sofia Coppola’s The Virgin Suicides, set in the 70s, “Playground Love” resonated with a new generation of sentimental high school sweethearts, and continues to do so. — JESSICA ROIZ
73. Janet Jackson, “Doesn’t Really Matter” (No. 1, Hot 100)
There’s a genuine charm in watching the outwardly glamorous Janet Jackson sing about inner beauty. Playing the love interest of Eddie Murphy in a fat suit in Nutty Professor II: The Klumps, Jackson co-wrote “Doesn’t Really Matter” for the film’s soundtrack. This breathy single, produced with Jimmy Jam and Terry Lewis, celebrates a love that transcends physical appearances. Set in a futuristic Tokyo, the music video, complete with sparkly gadgets and a robot dog, further enhanced the song’s appeal, making it Jackson’s first Hot 100 No. 1 of the 2000s. Decade aside, Ms. Jackson remains timeless. — DANICA DANIEL
72. Deftones, “Change (In the House of Flies)” (No. 3, Alternative Songs)
The music video for Deftones’ biggest hit, “Change (In the House of Flies),” perfectly captures the song’s atmosphere: mysterious, beautiful, seductive, and subtly menacing. Set at a seedy Hollywood party seemingly on the verge of chaos, the video complements the track’s unsettling vibe. Chino Moreno’s vocals, sounding almost submerged, contribute to the song’s haunting quality. “Change” offered a nu-metal horror that prioritized unnerving suggestion over jump scares, possessing less pop impact than Limp Bizkit but proving far more enduring two decades later. — A.U.
71. Savage Garden, “I Knew I Loved You” (No. 1, Hot 100)
Savage Garden enjoyed immense popularity in Southeast Asia, particularly in ballad-loving karaoke havens like the Philippines. “I Knew I Loved You,” with its sentimental lyrics, was an irresistible choice for radio, weddings, and karaoke sessions. Its universal appeal propelled it to become the duo’s second No. 1 hit on the Hot 100. The music video, featuring Darren Hayes reaching for Kirsten Dunst on a subway, added to the song’s romantic charm. — MIA NAZARENO
Image alt text: Savage Garden’s Darren Hayes and Kirsten Dunst in “I Knew I Loved You” music video, portraying a classic romantic ballad scene.
70. Fuel, “Hemorrhage (In My Hands)” (No. 30, Hot 100)
Two decades later, it’s remarkable that Fuel’s “Hemorrhage” became a crossover hit on pop radio, reaching No. 22 and the Hot 100 top 40, especially in today’s pop and hip-hop dominated charts. This post-grunge ballad, “Hemorrhage (In My Hands),” resonated deeply with listeners, with frontman Carl Bell’s lyrics inspired by his grandmother’s cancer diagnosis and passing. The powerful singalong chorus, regardless of lyrical understanding, became a rock radio staple, spending 12 weeks at No. 1 on Billboard‘s Alternative Songs chart. — XANDER ZELLNER
69. Incubus, “Stellar” (No. 2, Alternative Songs)
To understand Incubus within the nu-metal landscape of 2000, follow Brandon Boyd’s instruction in “Stellar”: “Meet me in outer space.” This enigmatic five-piece presented a surrealist vision for the genre. “Stellar’s” serpentine melody disguised math-rock elements as metal, while its distorted chorus belied a tender love song at its core. “Stellar” proved to have lasting impact, partially due to its embrace by the Guitar Hero generation, as the mainstream rock resurgence began to fade. — BRYAN KRESS
68. Marc Anthony, “You Sang to Me” (No. 2, Hot 100)
“You Sang to Me” should still come with a warning about listening when emotionally vulnerable. This breathtaking ballad is both gorgeous and heartbreaking. A massive hit, peaking at No. 2 on the Hot 100 and topping the Adult Contemporary chart for seven weeks, “You Sang to Me” is defined by its subtle sentimental touches: weeping acoustic guitars, a stately accordion solo, and Anthony’s stirring a cappella coda. The emotion is truly mutual. — C.P.
67. Toni Braxton, “He Wasn’t Man Enough” (No. 2, Hot 100)
After dominating the 90s with top 40 and adult contemporary hits, Toni Braxton returned in March 2000 with “He Wasn’t Man Enough.” This upbeat Darkchild production fit perfectly on pop and R&B radio, following similar-themed hits by TLC and Destiny’s Child. While the song begins with Braxton dismissively observing her ex’s new partner, her condescension evolves into thoughtful protectiveness. This female-empowering approach is highlighted in the music video, which is quintessential Y2K in its styling, futuristic lighting, and set design. — 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.” This warm, melancholic folk song, the second single from his breakout album White Ladder, became Gray’s signature track at the turn of the millennium. Layered with harmonious flourishes, Gray’s vocals dance over the melody, delivering emotional impact. “Babylon” captures a feeling of surrender and release in the face of a fading relationship in London, considered a modern-day Babylon, blending subtle electronic elements with insightful lyrics. — P.B.
Image alt text: David Gray performing “Babylon” music video, capturing the melancholic and introspective mood of the song.
65. BBMak, “Back Here” (No. 13, Hot 100)
British trio BBMak arrived amidst the boy band craze, offering a slightly different approach – while still attractive and harmonizing, they also played instruments. However, authenticity concerns are irrelevant to the quality of “Back Here,” a soft, gorgeous pop track with a remarkably delicate bridge. Peaking at No. 13 on the Hot 100, “Back Here” has remained a charming staple on adult contemporary radio for decades. — J. Lipshutz
64. Madonna, “Don’t Tell Me” (No. 4, Hot 100)
Throughout her career, Madonna often followed a flashy lead single with something more nuanced yet equally compelling. Such was the case with her Music era. After the electro-pop euphoria of the title track, “Don’t Tell Me” emerged as a twangy act of defiance. Featuring clipped vocals, guitar loops, strings, and a mainstream take on folktronica, “Don’t Tell Me” remains a forward-thinking and enduring track. — J. Lipshutz
63. Peaches, “F–k the Pain Away” (Did not chart)
Before Cupcakke, before “My Neck, My Back,” and before streaming services loosened radio censorship, there was “F–k the Pain Away,” a song so explicitly sexual it became a proto-meme. But beyond its shock value, it’s an excellent track – direct, minimalist, anchored by buzzing bass and percussive claps. “F–k the Pain Away” feels surprisingly contemporary two decades later, a testament to Peaches’ visionary artistry. — WILL GOTTSEGEN
62. SR-71, “Right Now” (No. 2, Alternative Songs)
SR-71’s debut single, “Right Now,” embodies the classic pop-punk sound that exploded in the early 2000s. Quickly embedding itself in pop culture through its use in the Dude, Where’s My Car? trailer and soundtrack, it became a stoner movie staple. From its unforgettable opening riff to the mid-song guitar solo and the “Bohemian Rhapsody” nod in the video, “Right Now” is a song that will forever evoke nostalgia for the Y2K pop-punk era. — BECKY KAMINSKY
61. Aaron Carter, “Aaron’s Party (Come Get It)” (No. 35, Hot 100)
Before life took a difficult turn for Aaron Carter, there was “Aaron’s Party (Come Get It),” a moment of pure pop joy. In the year 2000, Nick Carter’s younger brother was establishing his own name with funky, guitar-driven pop-rap. It was a simpler time, where grounding was the ultimate punishment. “Aaron’s Party,” the title track of his 3x platinum album, released when he was just 12, remains a charming and witty tale for the ages. — GAB GINSBERG
Image alt text: Aaron Carter in “Aaron’s Party” music video, capturing the youthful energy of early 2000s teen pop.
60. Enrique Iglesias, “Be With You” (No. 1, Hot 100)
Enrique Iglesias’ “Be With You” became his second No. 1 on the Billboard Hot 100, following “Bailamos,” and topped the chart for three weeks. This timeless song, expressing heartbroken yearning, became a classic. Featured on his eponymous 1999 bilingual album, “Be With You” was his formal introduction to mainstream America, winning hearts with English lyrics and his soaring chorus, “Now that you’re gone/ I just wanna be with you.” — GRISELDA FLORES
59. At the Drive-In, “One Armed Scissor” (No. 26, Alternative Songs)
“One Armed Scissor” is defined by dissonance – Cedric Bixler-Zavala’s barked vocals contrasted with Jim Ward’s Warped Tour-ready chorus, jarring time signature shifts, and the interplay between Ward and Omar Rodriguez-Lopez’s guitar riffs. The song’s complex and dynamic structure, somehow cohesive despite its disparate parts, foreshadowed At the Drive-In’s brief but impactful peak and subsequent demise less than a year later. — K.R.
58. No Doubt, “Simple Kind of Life” (No. 38, Hot 100)
After the assertive confidence of Tragic Kingdom‘s “Just a Girl,” Gwen Stefani revealed a more introspective side with “Simple Kind of Life,” the second single from No Doubt’s Return of Saturn. Wondering if she was better suited to a simpler life despite fame and success, Stefani explored themes of heartbreak not from a bad relationship (she had begun dating Gavin Rossdale) but from a demanding career, even contemplating accidental pregnancy to make life decisions for her. “You seem like you’d be a good dad” never sounded so poignant. — A.U.
57. Ja Rule feat. Lil Mo & Vita, “Put It on Me” (No. 8, Hot 100)
While Ja Rule and Vita were featured on the Rule 3:36 album version of “Put It on Me,” it was Lil Mo’s soaring ad-libs that propelled the remix to mainstream success. A quintessential ride-or-die anthem, “Put It on Me” (Remix) not only solidified Ja Rule’s signature crooning style within hip-hop but also established his credibility as a hitmaker in the 2000s. — C.L.
56. Mya, “Case of the Ex (Whatcha Gonna Do)” (No. 2, Hot 100)
Mýa was known for masking sharp digs within sweet melodies, as seen in 1998’s “Movin’ On.” However, she reached a new level of sass with “Case of the Ex.” Expressing frustration with her partner’s lingering contact with a past flame (“There’s no need to reminisce ’bout the past/ Obviously, cause that s–t did not last”), Mýa, with Tricky Stewart’s edgy production, resonated with women’s frustrations, propelling “Case of the Ex” to No. 2 on the Hot 100 by the end of 2000. — B.G.
Image alt text: Mya performing “Case of the Ex” music video, showcasing the confident and sassy attitude of 2000s R&B.
55. Common, “The Light” (No. 44, Hot 100)
In the often bleak and aggressively macho hip-hop landscape of the early 2000s, Common chose a different path with “The Light.” From his major label debut Like Water For Chocolate, “The Light” feels like a continuation of the conscious rap era of the 90s, featuring chivalrous rhymes reminiscent of love poems, fitting the song’s letter format. Inspired by Erykah Badu, produced by J Dilla (sampling Bobby Caldwell), and influenced by the nascent neo-soul movement, “The Light” offered a brighter perspective within a changing rap scene. — B. Kress
54. SoulDecision feat. Thrust, “Faded” (No. 22, Hot 100)
Amidst the boy band phenomenon, Canadian group SoulDecision snuck in a disco-pop hit into the Hot 100 top 40 with “Faded.” Their Brad Pitt-esque frontman and frosted tips aligned perfectly with the TRL aesthetic. While somewhat forgotten today and unavailable on streaming platforms, “Faded’s” funky bassline and cheeky lyrics deserve recognition. — K.A.
53. Creed, “With Arms Wide Open” (No. 1, Hot 100)
Creed perfected the post-grunge mid-tempo ballad, and “With Arms Wide Open” is arguably their finest example. While various radio edits exist, the original version is already emotionally charged, thanks to Scott Stapp’s lyrics about the surprise of impending fatherhood. “With Arms Wide Open” and “Higher” are strategically placed back-to-back on Human Clay, highlighting Creed’s ballad prowess. — K.R.
52. Dream, “He Loves U Not” (No. 2, Hot 100)
Dream’s debut album was titled It Was All a Dream, but this girl group was far from dreamy. Signed to Puff Daddy’s Bad Boy Records, Dream delivered slick pop R&B, achieving their biggest success with “He Loves U Not.” This funky tell-off track showcases the singers’ confidence in their man’s loyalty, daring another woman to try and steal him. The music video, featuring sassy attitudes, matching outfits, and dune buggy rides, further reinforced their self-assured image. — CHRISTINE WERTHMAN
51. Green Day, “Minority” (No. 1, Alternative Songs)
Don’t be misled by the acoustic guitar intro of Green Day’s “Minority” from Warning. This track quickly evolves into a rebellious call for individuality, incorporating harmonica and accordion for a unique flavor. While not Green Day’s most explicitly political song, “Minority” remains hard to resist, urging listeners to embrace their individuality. — J.G.
Image alt text: Green Day performing “Minority” music video, showcasing the band’s energetic and rebellious spirit in 2000.
50. Bloodhound Gang, “The Bad Touch” (No. 52, Hot 100)
In 2000, “The Bad Touch” was unlike any other radio hit – strange, overtly sexual, and incredibly catchy. This track, celebrating mating rituals by Pennsylvania’s Bloodhound Gang, blended spoken-word lyrics, NSFW themes, funk guitar, and club production into a crossover hit. Packed with pop culture references and humorous double entendres, “The Bad Touch’s” unexpected popularity was further boosted by Eminem’s reference in “The Real Slim Shady.” — K.B.
49. Son by Four, “A Puro Dolor” (No. 26, Hot 100)
A true Latin pop classic, Son By Four’s “A Puro Dolor” explores themes of unconditional love, heartbreak, and longing. “Give me back my fantasies and the courage I need to live,” the group sings in heartfelt Spanish lyrics. Such was its success, the group’s self-titled album featured three versions of the song – Spanish, English, and Salsa – cementing its timeless appeal. “A Puro Dolor” topped the Hot Latin Songs chart for a record-breaking 20 weeks and reached the Hot 100 top 40. — J.R.
48. Third Eye Blind, “Never Let You Go” (No. 14, Hot 100)
Between 1997 and 2000, Third Eye Blind was a dominant force in pop-rock. Following three top 10 Hot 100 hits from their debut album, “Never Let You Go,” from their second album Blue, surpassed them in pop culture longevity (except perhaps “Semi-Charmed Life”). Built around a recognizable guitar riff and an anthemic spoken-word ending, Stephan Jenkins sings about a doomed relationship he can’t accept. Decades later, its angst remains relatable, inspiring a recent cover by RAC and Hilary Duff. — X.Z.
47. Lonestar, “Amazed” (No. 1, Hot 100)
“Amazed,” one of modern country’s greatest love songs, proved its power both musically and personally. Penned by Aimee Mayo, Chris Lindsey, and Marv Green amidst candlelight, “Amazed,” from Lonestar’s Lonely Grill, immediately reached No. 1 on Billboard’s Hot Country Songs chart for eight weeks – and Mayo and Lindsey later married. This heartfelt ballad, with lyrics like “I want to spend the rest of my life, with you by my side,” continues to be a popular wedding song, evoking feelings of lasting love. — D.D.
46. Red Hot Chili Peppers, “Otherside” (No. 14, Hot 100)
Red Hot Chili Peppers aren’t primarily known for harmonies, but “Otherside” highlights the winning vocal combination of Anthony Kiedis and John Frusciante. Their blended vocals in the chorus are fitting for the song’s serious subject matter: a tribute to fallen guitarist Hillel Slovak and their own struggles with addiction. Flea’s melodic bassline also deserves recognition in this career highlight. — K.R.
Image alt text: Red Hot Chili Peppers performing “Otherside” music video, reflecting the song’s somber and introspective themes.
45. Vitamin C, “Graduation (Friends Forever)” (No. 38, Hot 100)
If you’ve attended a graduation in the past two decades, you’ve likely heard the chorus of Vitamin C’s “Graduation (Friends Forever).” Interpolating Pachelbel’s “Canon In D” and paired with lyrics pondering post-graduation anxieties, “Graduation” has become the bittersweet soundtrack to commencement ceremonies, offering a fresh, pop twist on graduation nostalgia. — RANIA ANIFTOS
44. Radiohead, “Optimistic” (No. 10, Alternative Songs)
“You can try the best you can/ The best you can is good enough” sounds initially positive, but carries a cynical undertone as the chorus of Radiohead’s dystopian anthem, “Optimistic.” The only radio hit from the landmark Kid A album, “Optimistic” trades positivity for unsettling sarcasm. Instead of ending on a hopeful note, it leaves us with the haunting realization that optimism may be futile. A fitting sentiment for uncertain times. — E.F.
43. LeAnn Rimes, “Can’t Fight the Moonlight” (No. 11, Hot 100)
The theme song for Coyote Ugly, “Can’t Fight the Moonlight,” boasts a sing-along chorus penned by Diane Warren and produced by Trevor Horn. However, LeAnn Rimes’ versatile vocals elevate this track from a bar anthem to something top-shelf. Her vocals range from whiskey lows to prosecco highs, showcasing her impressive vocal dexterity. — J. Lynch
42. The Avalanches, “Since I Left You” (Did not chart)
Like much of The Avalanches’ music, “Since I Left You,” from their 2000 album of the same name, is both lighthearted and subtly experimental. A psychedelic collage of pop sounds, it samples everything from pitched-up soul to warped jazz guitar into a celebratory jam. “Since I Left You” masks heartbreak with humor and hope, creating a dizzying, pastel sonic universe. — W.G.
41. Vertical Horizon, “Everything You Want” (No. 1, Hot 100)
How did Vertical Horizon’s “Everything You Want,” a relatively understated alternative rock single, reach the top of the Hot 100 in July 2000? Few alternative rock songs of that era were as emotionally resonant. Matt Scannell sings about a woman’s inexplicable lack of love, before shifting perspective to the man in the final chorus. The song’s bobbing guitar line and powerful chorus create a sense of frustration and longing, making it one of the strongest tracks of the year. — J. Lipshutz
Image alt text: Vertical Horizon performing “Everything You Want” music video, capturing the emotional intensity of the early 2000s rock ballad.
40. Christina Aguilera, “Come on Over Baby (All I Want Is You)” (No. 1, Hot 100)
Christina Aguilera solidified her place in teen-pop royalty with her self-titled debut album in 1999. “Come On Over Baby (All I Want Is You),” the album’s third single, became a Radio Disney-approved bop, inspiring a generation to sing into their hairbrushes. Danceable and addictive, it became her third consecutive Hot 100 No. 1, fueling the enduring Christina vs. Britney debate. — M.N.
39. U2, “Beautiful Day” (No. 21, Hot 100)
Despite its ubiquity in early 2000s pop culture, U2’s “Beautiful Day” surprisingly never cracked the Hot 100 top 20. However, this lead single from All That You Can’t Leave Behind has stood the test of time, becoming an anthem of inspiration and hope. Its uplifting message and pulsing rhythm invite listeners to embrace the outdoors, even while maintaining social distance. — J.G.
38. Jay-Z, “I Just Wanna Love U (Give It 2 Me)” (No. 11, Hot 100)
With its infectious beat and playful verses, Jay-Z’s “I Just Wanna Love U” became his first No. 1 on the Hot R&B/Hip-Hop Songs chart and reached No. 11 on the Hot 100. This track also propelled The Neptunes’ rise, produced by them with a chorus sung by Pharrell Williams. Jay-Z even gave them a shoutout in the lyrics, solidifying their influence. — T.C.
37. Bon Jovi, “It’s My Life” (No. 33, Hot 100)
By 2000, Bon Jovi had already achieved 15 years of hits. With Crush, they earned the right to be self-referential. “It’s My Life,” a comeback anthem, references Tommy and Gina from “Livin’ on a Prayer,” their working-class heroes from 1986. Over a decade later, “It’s My Life” celebrated their enduring spirit, introducing a new generation to fist-pumping stadium rock. — K.B.
36. Mystikal, “Shake Ya Ass” (No. 13, Hot 100)
Mystikal, from No Limit Records, secured his first crossover hit with “Shake Ya Ass.” Featuring an irresistible Neptunes shuffle and two knockout choruses, one by Mystikal and one by a sweet-falsetto vocalist, the track left no room for doubt. Mystikal’s verses matched the energy, making “Shake Ya Ass” a defining track of early 2000s hip-hop. — A.U.
Image alt text: Mystikal performing “Shake Ya Ass” music video, capturing the high-energy and raw intensity of the song.
35. Santana feat. The Product G&B, “Maria Maria” (No. 1, Hot 100)
Legend has it, Wyclef Jean conceived “Maria Maria” after hearing Wu-Tang Clan’s “Wu-Tang Clan Ain’t Nuthing ta F’ Wit.” He transformed its menacing riff into a summer anthem, anchored by Santana’s Latin guitar and The Product G&B’s smooth vocals. Topping the Hot 100 for 10 weeks and winning a Grammy, “Maria Maria” later returned to the charts via DJ Khaled’s “Wild Thoughts,” but nothing compares to Santana’s original seductive guitar notes. — B.G.
34. Nine Days, “Absolutely (Story of a Girl)” (No. 6, Hot 100)
Remember when power pop songs reached the Top 10? In 2000, Nine Days’ “Absolutely (Story of a Girl)” peaked at No. 6 on the Hot 100, driven by its undeniable singalong chorus. Whether about lead singer John Hampson’s current or past girlfriend, the song about her winning smile remains impactful. “Absolutely” maintains its legacy through TikTok and in the hearts of Y2K pop-rock fans. — G.G.
33. Backstreet Boys, “Shape of My Heart” (No. 9, Hot 100)
How do you follow up a boy band classic? While Backstreet Boys couldn’t surpass “I Want It That Way,” “Shape Of My Heart,” the lead single from Black & Blue, came close. From the opening guitar strum, it evokes emotion, escalating to a climactic chorus. “Shape Of My Heart,” with its heartfelt lyrics and punchy production, is charmingly cheesy BSB at its best, even if its message is slightly clearer than “That Way.” — T.W.
32. Alice Deejay, “Better Off Alone” (No. 27, Hot 100)
If ringtones existed in the early 2000s solely for “Better Off Alone’s” synth hook, it would have been justified. This iconic riff became the “(I Can’t Get No) Satisfaction” of turn-of-the-millennium electro-pop. Play it loud, dance-cry to it, or tap it out anywhere – it’s a riff for all occasions, deeply ingrained in our cultural DNA. Judith Pronk’s vocals wring surprising emotion from just ten words: “Do you think you’re better off alone?/ Talk to me.” — A.U.
Image alt text: Alice Deejay in “Better Off Alone” music video, emphasizing the iconic synth hook and early 2000s electronic dance music vibe.
31. Britney Spears, “Lucky” (No. 23, Hot 100)
While not the first song that comes to mind from Oops!…I Did It Again, Britney Spears’ “Lucky” is a standout track. “Lucky” uses music to comment on the challenges of fame and isolation, all while remaining danceable. Both heartbreaking and campy, “Lucky” showcases Britney at her most self-aware, even within a seemingly simple story about “a girl named Lucky.” — S.D.
30. Lee Ann Womack, “I Hope You Dance” (No. 14, Hot 100)
“I Hope You Dance” deservedly won numerous country music awards. This touching ballad avoids excessive sentimentality, delivering a message of hope and aspiration. While open to interpretation, it’s often seen as a parent’s wish for their child. Gladys Knight covered it in 2013, but Lee Ann Womack’s original version with Sons of the Desert remains definitive. — PAUL GREIN
29. Wheatus, “Teenage Dirtbag” (No. 7, Alternative Songs)
Amidst cocky pop-punk bands dominating TRL, Wheatus offered a more relatable alternative with “Teenage Dirtbag,” an anthem for underdogs. Brendan B. Brown’s androgynous vocals introduce the dreamy Noelle, whose “boyfriend’s a d–k.” The heartsick teen gets the girl through a shared love of Iron Maiden. Featured on the Dawson’s Creek soundtrack, it better fit the spirit of Freaks and Geeks. — C.W.
28. Faith Hill, “The Way You Love Me” (No. 6, Hot 100)
While discussions persist about female representation on country radio, 20 years ago, artists like Faith Hill thrived. “The Way You Love Me,” blending country, pop, and dance elements, colorful lyrics, and Hill’s exuberant vocals, perfectly captures the euphoria of love. It stood alongside Reba McEntire, Martina McBride, and Shania Twain as a prominent female voice in country music. — G.M.
Image alt text: Faith Hill in “The Way You Love Me” music video, radiating the joyful and energetic vibe of early 2000s country pop.
27. 3 Doors Down, “Kryptonite” (No. 3, Hot 100)
The Kinks wished to fly like Superman; Our Lady Peace declared him dead. As post-grunge extended into the millennium, 3 Doors Down, an unknown band from Mississippi, entered rock’s Superman canon and triumphed. “Kryptonite” became ubiquitous on rock and pop radio, with Brad Arnold’s relatable lyrics about superhuman strength and its absence resonating widely. — C.P.
26. Dr. Dre feat. Eminem, “Forgot About Dre” (No. 25, Hot 100)
In case anyone “Forgot About Dre” during his seven-year hiatus, he and Eminem delivered a powerful reminder with “Forgot About Dre” from 2001. “Still the same O.G./ But I been low-key,” Dre asserts, before listing his accomplishments. Eminem’s Slim Shady persona also makes a memorable appearance, defending Dre’s legacy against critics. The Grammy-winning track re-established Dr. Dre’s enduring influence. — A.C.
25. Ludacris feat. Shawnna, “What’s Your Fantasy” (No. 21, Hot 100)
Ludacris burst onto the scene with “What’s Your Fantasy,” a breakthrough hit filled with attention-grabbing, salacious lyrics. His punchline-heavy style showcased his verbal creativity and dexterity. Three years before Lil Jon & the Eastside Boyz’s “Get Low,” Ludacris was pushing lyrical boundaries and establishing himself as a leading MC of the early 21st century. — A.U.
24. Destiny’s Child, “Jumpin’ Jumpin’” (No. 3, Hot 100)
Destiny’s Child essentially invented the club with “Jumpin’ Jumpin’,” the infectious soundtrack to a girls’ night out. Beyoncé co-produced this upbeat track, the final single from The Writing’s on the Wall, laying the foundation for her solo sound and powerful presence. “Jumpin’ Jumpin'” remains a timeless anthem for female empowerment and confident independence. — T.C.
Image alt text: Destiny’s Child performing “Jumpin’ Jumpin'” music video, showcasing the energetic and empowering girl group vibe of 2000s R&B.
23. Moby, “Porcelain” (No. 18, Hot 100)
Moby’s music seemed to predict the sound of the new millennium, and “Porcelain,” from his electronica masterpiece Play, gained traction at the turn of the century. With reversed strings, piano melody, and ethereal vocals, “Porcelain” created a groundbreaking sonic experience, pushing genre boundaries. While Moby’s fame became somewhat of a punchline later, “Porcelain” remains a timeless example of his innovative artistry. — B. Kress
22. Blink-182, “Adam’s Song” (No. 2, Alternative Songs)
“Adam’s Song,” while not the first of its kind, directly addressed mental health in a way that resonates even more powerfully today. While topics like suicide and depression aren’t new, discussions around them are less taboo now. “Adam’s Song,” a slower, more introspective track compared to “What’s My Age Again” and “All the Small Things” from Enema of the State, features poignant lyrics like “please tell mom this is not her fault,” making it one of Blink-182’s most impactful songs. — J.G.
21. Sisqo, “The Thong Song” (No. 3, Hot 100)
“The Thong Song” defied convention in many ways. Sisqo sang about thongs with a passion usually reserved for love or revenge, repeated the same verse three times, and incorporated Ricky Martin references and cheesy lines. In 2020, it might seem absurd, but in 2000, “The Thong Song” was a booty-shaking phenomenon, reaching No. 3 on the Hot 100. — C.L.
20. Eminem, “The Real Slim Shady” (No. 4, Hot 100)
Eminem, as always, targeted perceived adversaries in “The Real Slim Shady,” the lead single from The Marshall Mathers LP. He lyrically attacked figures from Tom Green to boy and girl groups. Despite mocking pop culture, “The Real Slim Shady” and its MTV-dominating video cemented Slim Shady’s place in pop, propelling him to the Hot 100 top five for the first time. — K.A.
Image alt text: Eminem in “The Real Slim Shady” music video, capturing the rebellious and satirical nature of the song in 2000.
19. Madonna, “Music” (No. 1, Hot 100)
Facing ageism in pop, Madonna needed a surefire hit to top the Hot 100 at 41. “Music,” her collaboration with Mirwais, delivered. A dancefloor anthem with electroclash elements for club-goers, a techno beat for ravers, and old-school electro-funk for older fans, “Music” brought people together across generations for Madonna’s third decade of pop dominance. — J. Lynch
18. *NSYNC, “It’s Gonna Be Me” (No. 1, Hot 100)
“It’s Gonna Be Me,” the second single from *NSYNC’s No Strings Attached, further established their confident attitude. A Max Martin co-written classic, produced by Rami Yacoub, it encourages self-worth and resilience. Culturally enduring, it’s become a meme associated with April 30th and Justin Timberlake’s “MAY” pronunciation. Beyond memes, “It’s Gonna Be Me” was *NSYNC’s only Hot 100 No. 1 hit. — B. Kaminsky
17. Papa Roach, “Last Resort” (No. 57, Hot 100)
Suicide has been a topic in music for decades, but Papa Roach’s “Last Resort” is uniquely intense. This pop-metal track, performed with raw anguish, from the opening line “Cut my life into pieces / this is my last resort!” to Jacoby Shaddix’s breakdown, conveys the urgency of a traumatic situation. “Last Resort” remains a profoundly cathartic take on a dark subject and arguably the finest single of the nu-metal era. — J. Lipshutz
16. Christina Aguilera, “What a Girl Wants” (No. 1, Hot 100)
Originally recorded by French singer Ophélie Winter, “What a Girl Wants” became Christina Aguilera’s second consecutive Hot 100 chart-topper. This glitchy, R&B-infused pop single, expressing gratitude for a patient boyfriend, was translated by Aguilera into a global hit. “What a Girl Wants” still evokes nostalgia for the late 90s/early 2000s pop era. — T.M.
Image alt text: Christina Aguilera in “What a Girl Wants” music video, showcasing the stylish and confident image of early 2000s pop divas.
15. Dixie Chicks, “Goodbye Earl” (No. 19, Hot 100)
After the ballad “Cowboy Take Me Away,” Dixie Chicks showcased their audacity with “Goodbye Earl.” Narrated by Natalie Maines, the banjo-tinged track graphically depicts an abusive marriage, but quickly becomes a tale of vengeance and murder. “Goodbye Earl” remains the Dixie Chicks’ boldest statement, thanks to its black-comedy lyrics and Maines’ fiery delivery, making it 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 of Aaliyah’s “Try Again.” This slinky, Timbaland-produced track from the Romeo Must Die soundtrack encourages perseverance in love. Timbaland’s signature “wiki-wiki” sounds are prominent, as in “Are You That Somebody?” “Try Again” became Aaliyah and Timbaland’s first Hot 100 No. 1, tragically cut short by Aaliyah’s untimely death a year later. — K.A.
13. Red Hot Chili Peppers, “Californication” (No. 69, Hot 100)
Ironically, “Californication,” Red Hot Chili Peppers’ meditation on Hollywood’s dark side, became one of their biggest hits. The title track is filled with cryptic lyrics and cultural references, sung over John Frusciante’s ominous guitar. Combined with its iconic fake-video game music video, “Californication” solidified RHCP’s continued relevance in the 2000s, and its “-ation” rhymes remain memorable. — T.C.
12. Dr. Dre feat. Snoop Dogg, “The Next Episode” (No. 23, Hot 100)
In 1999, Dr. Dre and Snoop Dogg created a sequel to “Nuthin’ but a ‘G’ Thang” for a new era. “The Next Episode,” with its iconic opening horns sampled from David Axelrod and David McCallum’s “The Edge,” marked a stylistic evolution. Moving beyond lowrider vibes, they created a slick West Coast sound that looked to the future while honoring its roots. The result was as inspired and timeless as “‘G’ Thang.” — W.G.
Image alt text: Dr. Dre and Snoop Dogg in “The Next Episode” music video, representing the iconic West Coast hip-hop duo in 2000.
11. Jay-Z feat. UGK, “Big Pimpin’” (No. 18, Hot 100)
Jay-Z in his brash Brooklyn playboy era, living life on the edge, is perfectly captured in “Big Pimpin’.” Refusing to commit in relationships, he brags about his stamina and lifestyle. Timbaland’s luxurious beat, Bun B’s timeless hook, and Pimp C’s verse create an iconic track that epitomizes early 2000s hip-hop extravagance. — C.L.
10. Nelly, “Hot (S***) Country Grammar” (No. 7, Hot 100)
Before Nelly’s debut album Country Grammar in June 2000, the Midwest had Eminem. Nelly, from St. Louis, offered a more celebratory Midwestern hip-hop sound. The title track, “Hot (S***
