90s Breakup Songs

The song that detonated Jagged Little Pill into a 33-million-selling phenomenon. Alanis turned a breakup into a full-body exorcism, and every woman who'd ever been wronged screamed along in her car.

Prince wrote it, but Sinead O'Connor owned it forever. That single tear rolling down her cheek in the video is one of music's most iconic images -- raw grief made universal.

A masterclass in storytelling that's made more people cry in traffic than any other song in history. Tracy Chapman walked onto the Wembley stage with an acoustic guitar and stopped the world.

Jewel lived in her van and wrote this devastating morning-after breakup song that spent 65 weeks on the Hot 100. Pieces of You went on to sell 12 million copies on the strength of tracks like this.

The first number-one hit by an artist without a record deal. Ethan Hawke passed the demo to Ben Stiller for the Reality Bites soundtrack, and Lisa Loeb became the bookish heartbreak icon of the 90s.

Hope Sandoval barely whispered, and it was the loudest thing in the room. This dream-pop masterpiece soundtracked every 90s teen drama's almost-kiss and still gives goosebumps on first listen.

So ubiquitous in the late 90s that it basically replaced oxygen in certain demographics. An Australian soap star turned a cover song into one of the decade's defining pop-rock heartbreak anthems.

Written about the heroin overdose of Smashing Pumpkins' touring keyboardist, this became one of the most emotionally devastating ballads of the decade -- and later, the ASPCA commercial that broke the internet.

The Dawson's Creek theme song that soundtracked a million teen melodramas. Paula Cole was nominated for seven Grammys that year, and this song became the emotional wallpaper of the late 90s.

Already huge in the UK when Eminem sampled it for 'Stan' and introduced her to every rap fan in America. A gorgeous, understated love letter that became a CMR staple through sheer emotional resonance.

Natalie Merchant left 10,000 Maniacs at peak fame and delivered this swirling, hypnotic lead single. Tigerlily was the album your cool English teacher played on the last day of school.

Inspired by Alice Walker's writing about female genital mutilation, Tori Amos turned betrayal between women into an art-rock puzzle box. The harpsichord-driven groove was unlike anything else on the radio.

A Christian alt-rock band made the most secular-sounding kiss anthem of the 90s. It floated through every rom-com trailer like a butterfly made of jangly guitars and pure dopamine.

Before she went full Timbaland pop, Nelly Furtado was making breezy, genre-defying folk-trip-hop. This whimsical debut single won a Grammy and captured peak early-2000s CMR energy.

That piano riff is tattooed on the collective consciousness. A classically trained pianist turned a walking-through-the-city daydream into the most triumphant commute song ever written.