30. No Doubt – “Bathwater”
With Return of Saturn, No Doubt proved its reign would be genre-bending. But “Bathwater” returned the Gwen Stefani-led group to their ska-reggae roots. Anchored by pulsating bass and thumping drums, the song flaunts a bouncy melody as the singer laments being drawn to a man who’s indifferent about her. Despite knowing about his ex-lovers, she continues to have an inexplicable affection for him, continuing to wash herself in his “old bathwater.” And the cycle persists. – I.K.
29. Destiny’s Child, “Independent Women”
The chart domination of “Independent Women” — one of only 39 songs (as of July 2020) to spend over 10 weeks at the No. 1 spot on the Billboard Hot 100 — was a literal surprise. The group’s manager (and Beyoncé’s father), Mathew Knowles, covertly submitted the song for inclusion on the Charlie’s Angels soundtrack, one year before the track (and its “Part II”) appeared on their third album, 2001’s Survivor. But the hit’s franchise framing soon became its least compelling aspect: It remains a lasting feminist manifesto to financial autonomy, the freedom to pay your own bills and the right to self-determination. – S.F.
28. Nelly Furtado, “I’m Like a Bird”
The Mellotron, an electro-mechanical keyboard invented in England in the ‘60s, is most closely associated with prog-rock and psychedelic songs like the Beatles’ “Strawberry Fields Forever.” But the instrument’s unmistakable quivering texture made an unlikely return to the pop charts in 2000 via the faux symphonic fanfare of Canadian singer’s Nelly Furtado’s debut hit. “I’m Like a Bird” offers an earthy singer-songwriter appeal. But the groovy synth work and the bassline by Dr. Dre’s right-hand man Mike Elizondo give the song a subtle R&B bounce that foreshadowed Furtado’s later, clubbier hits with Timbaland. – A.S.
27. Blink-182, “Man Overboard”
“Man Overboard” was an odd man out during the Enema of the State sessions in 1999. The now-beloved tune wasn’t finished in time for the record and was instead tacked on as a promo single for The Mark, Tom, and Travis Show (The Enema Strikes Back!), their subsequent live record. The rumbling track is one of Blink’s best: addictive, aggressive and full of instantly recognizable hooks, like Mark Hoppus’ opening bass riff and Tom DeLonge’s chugging guitar melody. Plus, everybody knows somebody who’s “out of line and rarely sober.” - B.O.
26. Godspeed You! Black Emperor, “Storm”
This is the dystopian future that Godspeed You! Black Emperor foretold; we’re just living in it. If 1997’s F# A# ∞ and 1999’s Slow Riot for New Zero Kanada set the pre-apocalyptic stage, Lift Your Skinny Fists Like Antennas to Heaven sends a Phoenix streaking through the ruins, mourning and vengeful in equal measure. Opener “Storm” swiftly achieves a self-immolating altitude — a conservatory rupture of pealing horns, incandescent strings, thermite guitars — then dips in and out of wind currents. When these mood-ring post-rock blues do desist, it’s to roll tape on an Orwellian service station recording that remains, two decades on, capable of raising the hairs on the back of necks. – R.C.
25. Madonna, “Don’t Tell Me”
After drawing all the club kids to the neon-hued dance floor with glitzy lead single “Music,” the Queen of Unpredictability decided to take listeners…back to the ranch? In an album filled with electronica, “Don’t Tell Me” stuck out like a twangy thumb ready to hitch a hike. In true Sheryl Crow-gone-wild fashion, Madonna grabbed her trusty Stetson hat and channeled her inner cowgirl. But it wouldn’t be Madonna without some experimental elements: a CD-skip stutter effect, orchestral strings, obscure lyricism (“Tell the bed not to lay / Like the open mouth of a grave”) and homegrown country guitars that flipped the genre on its head while scoring her yet another top-five hit. – B.G.
24. Coldplay, “Shiver”
Before they became one of the biggest bands on Earth and collaborated with Rihanna and the Chainsmokers to maintain their Top 40 market share, Coldplay were just another post-Britpop band who aspired to the swooning falsetto dramatics of Jeff Buckley and Thom Yorke. Released as the first single from Parachutes in the U.K. and the second single in the U.S., “Shiver” was less successful than “Yellow” in both markets but better crystallized the band’s sound at the time. The winsome melody and 6/8 gallop echo Buckley’s “Grace” and Radiohead’s “(Nice Dream)” enough to make Chris Martin’s influences transparent. But Johnny Buckland’s soaring lead guitar and Will Champion’s propulsive drums, which would get lost in the mix more and more in the band’s quest for world domination, have never sounded better than they did on “Shiver.” – A.S.
23. Smashing Pumpkins, “The Everlasting Gaze”
Wounded, dramatic and declaratory, “The Everlasting Gaze” packs a lot of punch; it had to, had to. The Smashing Pumpkins were a fallen Icarus in that moment — there’d been losses and evasions and an entire pop culture universe that spun away from their orbit since the triumph of 1995’s Mellon Collie and the Infinite Sadness. So the guitars of Billy Corgan and James Iha are blaring and overdriven; drummer Jimmy Chamberlin lays on a mighty thwomp; and Flood produces with a crushing, mythic intensity. This is that “Zero”/“Jellybelly,” no fucks given near-metal shit; the vocals claw straight down to your soul, never letting go. – R.C.
22. Mystikal, “Shake Ya Ass”
The early ‘00s club scene would be even quieter than 2020’s without the Neptunes’ influence on airwaves. The production duo of Chad Hugo and Pharrell Williams changed the pop and hip-hop landscape with an unmistakable dash of funk in everything they touched — they really cruised into the new millennium looking like Clipse’s Lord Willin’ cover. Their first triumph of 2000 was Mystikal’s “Shake Ya Ass,” a song that can transform any setting into a twerking triathlon. Seriously, throw this bad boy on at a Sam’s Club and try not to bust it down once that bassline hits and Mystikal demands that you show him what you’re working with. – B.B.
21. *NSYNC, “Bye Bye Bye”
Some songs are their own moments. And for *NSYNC, “Bye Bye Bye” represented freedom. The masterfully choreographed boy band’s best-selling album, No Strings Attached, followed a tedious legal battle with former management; and though the lyrics to its lead single focus on a romantic breakup, it’s hard not to interpret both titles in their historical context — as the pitch-perfect quintet cutting off their puppet strings and bidding their past farewell. “Bye Bye Bye” channeled the best of Y2K pop and gave Justin Timberlake that massive chorus to propel him into eventual ramen-hair superstardom. It’s also a reminder that JC Chasez was (and remains) a powerhouse, crushing an opening verse we still hold close to our Team JC hearts. – B.B.
20. Erykah Badu, “Bag Lady”
One of the music industry’s favorite bait-and-switch schemes peaked around the year 2000: The biggest hit from an album was often a remix that sounded completely different from the version you’d hear when you bought the physical product. On Erykah Badu’s lush, ambitious second LP, Mama’s Gun, “Bag Lady” was a slow burner with delicate snare drum rolls, electric piano and a guitar line borrowed from Dr. Dre’s “Xxplosive” interpolation of “Bumpy’s Lament” by Isaac Hayes. But the version featured in the video that pushed the song to No. 6 on the Hot 100 was “Bag Lady (Cheeba Sac Radio Edit),” which swapped out Badu’s live band arrangement for the thumping beat from the widely sampled Dr. Dre track. Eventually, Motown gave consumers what they were looking for, reissuing Mama’s Gun in 2001 with the “Bag Lady” remix as a bonus cut. – A.S.
19. Mya, “Case of the Ex”
Mya was briefly everywhere around the turn of the century: making hits with everyone from Jay-Z to Silkk the Shocker, singing hooks for Pras and Beenie Man, joining the all-star “Lady Marmalade” remake that topped the charts in 2001. But “Case of the Ex” was the one big moment where she stood on her own, interrogating a boyfriend who’s just a little too friendly with an ex. It’s the kind of classic R&B scenario that usually makes for great ballads, but producer Tricky Stewart filled “Case of the Ex” with intricate drum patterns that primed the track for crossover success, almost a decade before he became a Billboard fixture with blockbusters like “Umbrella” and “Single Ladies.” In the video, Mya and her friends do synchronized dance moves with big metal pipes in the middle of the desert, like they’re about to throw down in some kind of choreographed Mad Max dystopia. But “Case of the Ex” resonated because of how well its lyric dramatized the ordinary everyday jealousy and paranoia that can accompany a young relationship. – A.S.
18. Craig David, “Fill Me In”
Everything about this R&B-dance banger feels distinctly Y2K: the staccato synth-strings, the sweet (if slightly sterile) drum programming, the goofy production techniques (the telephone EQ on “Please leave a message after tone”). But even if “Fill Me In,” the signature hit from the British singer’s debut LP, sounds a bit dated two decades later, the song itself still rips. David’s nimble rhythmic twists in the first verse are God-level: “So I went in, then we sat down, start kissing, caressing / Told me about jacuzzi, sounded interested, so we jumped right in.” – R.R.
17. Linkin Park, “In the End”
“In the End” has remained Linkin Park’s signature song for two decades. Fusing hard rock riffs, rapped verses and ballad-level introspection, “In the End” — the final single off Linkin Park’s 2000 debut, Hybrid Theory — helped set the group apart from the Limp Bizkits of the early aughts. The enchanting piano line opens the track before erupting into an explosive, existential chorus rooted in defeat. “I tried so hard and got so far / But in the end, it doesn’t even matter,” singer Chester Bennington screams in raw angst. And Bennington did get far: “In the End” is an integral part of the band’s legacy. – I.K.
16. Dashboard Confessional, “Screaming Infidelities”
At the turn of the century, Dashboard Confessional played a key role in the progression of emo with the slow-burning heartbreak anthem “Screaming Infidelities.” Released on the band’s independent debut, The Swiss Army Romance, the tearjerker put a vulnerable lens on a relationship’s demise from unfaithfulness. Despite the fallout, singer Chris Carrabba can’t help but find reminders all around: “Your hair is everywhere / Screaming infidelities, and taking its wear.” The piercing chorus wail lives on as a fan-favorite sing-along for a reason. – I.K.
15. Sunny Day Real Estate, “One”
By Y2K, Sunny Day Real Estate were no longer the emo darlings of their 1994 debut, Diary. The band’s trajectory in the six years between is the stuff of lore: the spiritual epiphany of frontman Jeremy Enigk, the lineup’s initial collapse and (partial) reunion, the gradual sonic evolution that crescendoed with their sadly underrated swan song, The Rising Tide. The album’s lush, symphonic sound and philosophical lyrics alienated the OG fans (and many critics) who clearly craved the basement-fidelity angst of “Seven” and “In Circles.” But Enigk’s songwriting blossomed on this grander scale, epitomized by the record’s sole single, “One.” Like their early work, it’s driven by the entangled distortion of Enigk and Dan Hoerner, with William Goldsmith’s fluid, lyrical drumming — full of articulate tom flourishes and swooshing open hi-hats — the not-so-secret MVP. But like many Rising Tide cuts, “One”’s earnest melodies and startling dynamic shifts approach a prog-like level of sophistication. – R.R.
14. Lifehouse, “Hanging By A Moment”
According to the 2000 U.S. Census, there were 71.8 million family households in America — and all of them contained at least one Lifehouse fan. Your mom, dad, little sister, guinea pig — there was someone who couldn’t get enough of “Hanging By A Moment,” one of the alt-rock wave’s biggest hits. The bounding jam, which frontman Jason Wade has said was written in roughly 10 minutes, climbed all the way to No. 2 on the Billboard Hot 100, fueled by massive crossover play on pop, rock and adult contemporary radio. Everybody loves a chorus, and Wade credits the simple melody, which he accurately describes as “almost nursery rhyme-ish,” as the key to the song’s success. But lest we forget that deep, opening note — not a cello but a bow drawn across an upright bass — which feels like an exhale and sets the tone for one of the greatest radio rock earworms of the last 20 years. – B.O.
13. Jay-Z, “I Just Wanna Love U (Give It 2 Me)”
The ‘90s was the Decade of Jay-Z, with the Brooklyn native showing the world why he was the dopest rapper in the game. But during that time, he didn’t really have a mainstream hit (save for 1998’s “Hard Knock Life”) in his back pocket. So who do rappers call when they want to cross over? The Neptunes, of course. “I Just Wanna Love U (Give It 2 Me),” the production duo’s first collaboration with Jay-Z, found Hov at his most playful, spitting about quintessential Y2K items: Chloe glasses, Cristal and two-way Motorola pagers. The infectious song was topped with Pharrell’s signature falsetto that still has everyone “in the club, high, singing off-key” to this day. – B.G.
12. A Perfect Circle, “Judith”
They had us at “fuck your God!” Named for Maynard James Keenan’s mother, “Judith” was the world’s explosive introduction to A Perfect Circle, a side-project that sounded a lot like Tool, only loaded with more digestible melodies and studio polish. The lead single from 2000’s dare we say, pretty, debut LP, Mer de Noms, played not unlike Tool’s breakthrough “Sober” — with a big, fat guitar riff and Keenan’s patently brooding lyricism, exploring his mother’s religious devotion even as her health deteriorated. The tune was also a major respite for Tool fans who’d been drooling since ‘96’s Ænima melted their brains. – B.O.
11. Nelly, “Country Grammar (Hot Shit)”
By the end of the ’90s, virtually every platinum-level rapper hailed from one of a few major cities with storied hip-hop scenes. Then Cornell Haynes stormed out of Missouri at the dawn of the new millennium and his debut album sold 10 million copies. Jason “Jay E” Epperson, a producer from Nelly’s hometown of St. Louis, gave “Country Grammar” such a bright, bubbly backing track that people almost didn’t notice that Nelly was rapping about a drive-by shooting and passing a joint. There were already plenty of vocalists who alternated between melodic vocals and staccato rhymes before Nelly, but Nelly’s sing-song flow bridged the gap between the Bone Thugs-n-Harmony era and the Drake era, helping break down the distinction between singing and rapping for good. – A.S.