13 items
A couple with nothing left in common grasps for one shared thing and lands on the Audrey Hepburn movie — "we both kinda liked it." The kicker: Todd Pipes actually wrote it about a different Hepburn film entirely. Earnest, hook-driven, and the only thing the world remembers Deep Blue Something for.
Written by guitarist Matt Slocum and sung by Leigh Nash, this track from Sixpence None the Richer's 1997 self-titled album went nowhere at first. Everything changed in early 1999 when Miramax picked it for She's All That and it landed on Dawson's Creek's soundtrack the same spring. The song detonated, peaking at No. 2 on the Billboard Hot 100 in May and becoming an instant 90s classic.
The Los Angeles radio-rock band behind "Hanging by a Moment" — a famous Billboard chart anomaly. Frontman Jason Wade's five-minute songwriting session produced a single that never hit weekly No. 1 yet finished as Billboard's No. 1 song of 2001. Earnest, huge-chorused, everywhere.
One of the biggest radio songs of the late '90s — and almost nobody knew it was a cover. Natalie Imbruglia's version went supernova in 1997, spending 11 weeks atop Billboard's airplay chart while barely denting the Hot 100, because you literally couldn't buy it as a US single. The video's film crew dismantled the apartment set around her mid-song.
The raspy-voiced anti-pop-star of the TRL era — the one who mocked the pop machinery while beating it at its own game. Missundaztood sold 13 million copies on pure attitude, and "Get the Party Started" is still doing exactly what it promised.
The breakup-scream anthem of the 2000s. Kelly Clarkson needed an identity beyond American Idol; Max Martin and Dr. Luke handed her a pop-rock chorus that demanded everything a voice could give, and every car ride since has been a rehearsal.
Somebody once told me — you know the rest. Smash Mouth's 1999 radio staple peaked at #4 on the Hot 100, but immortality arrived in 2001, when it played over Shrek's opening credits and fused itself permanently to a green ogre. The internet did the rest.
"This is the story of a girl, who cried a river and drowned the whole world" — the hook that owned the radio in summer 2000, peaking at No. 6 on the Billboard Hot 100. Singer John Hampson wrote it about his then-girlfriend (later his wife) after an argument before a concert. The follow-ups never matched it, but the hook never left.
The Long Beach ska-punk legends who put out their early records on Skunk Records, their own DIY imprint, and whose sun-drenched sound against a backdrop of tragedy became the whole story. They broke nationally in 1995 with "Date Rape" on LA's KROQ, but the songs everyone remembers—"What I Got," "Santeria," "Wrong Way"—arrived after Bradley Nowell's heroin overdose in May 1996, two months before the album that contained them.
The funk-metal band that flipped into sunshine pop overnight with "Fly" in 1997—a reggae-tinged groove with bleak lyrics about death wrapped in an impossibly breezy hook, with Mark McGrath's frosted tips becoming the era's defining haircut. They owned the radio from 1997 to 2001—"Every Morning," "Someday," "When It's Over"—then eased into the fade, with McGrath resurfacing as a celebrity-news host on Extra.
![Video thumbnail — Sugar Ray - Fly [Official Video]](https://i.ytimg.com/vi/cxHkD7rUm_Q/hqdefault.jpg)
The song that flipped a funk-metal band into sunshine pop overnight—bleak lyrics about death and loss wrapped in a breezy reggae-tinged groove, with Mark McGrath's frosted tips as the era's defining haircut. It owned the radio all summer and never touched the Hot 100.
An outcast anthem in a nasal falsetto: the kid with the AC/DC tapes everyone treated like a devil worshipper, pining for a girl out of his league. The twist — "two tickets to Iron Maiden, baby" — is one of pop's great reveals. America shrugged; the rest of the world made it enormous.
"Just go ahead now": the jangly riff every '90s kid can hum and the band name most of them can't produce. It made VH1's greatest-songs-of-the-'90s list and Blender's worst-songs-ever list — and honestly, both lists have a point.