3 Timeless Breakup Songs From the 1990s

Breakup songs are as old as songwriting. But artists in the 90s really put their fee-fees on full display. The whole point of being human is connection, and while many songwriters have felt like outsiders, the rejection from a breakup is felt by everyone. The tracks below were each massive hits, and they remain classics because sadness doesn’t age.

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“You Oughta Know” by Alanis Morissette

There aren’t many songs expressing the enduring bitterness of a bad breakup like Alanis Morissette’s grunge-pop anthem. The track features a dark funk groove from Flea and his then-bandmate in the Red Hot Chili Peppers, Dave Navarro. Meanwhile, Morissette seethes toward her ex, and with how popular this song became, you have to feel for the poor sap that broke her heart. Morissette has some … questions for her ex, whom she calls Mr. Duplicity. No need to repeat the most scathing lines, but when she says how he promised to hold her until he died, “but you’re still alive!”—Mr. Duplicity, indeed.

“Stay (I Miss You)” by Lisa Loeb

The soundtrack to Reality Bites opens with “My Sharona”, and if you’ve seen the movie, you know exactly why. But there’s a quiet little tune that did quite a bit of heavy emotional lifting in the 90s, Lisa Loeb’s “Stay”. In the film, Ethan Hawke portrays Troy Dyer, who became an avatar for Gen X angst and cynicism. But Hawke, who was Loeb’s neighbor, also gave her song to Ben Stiller, which led to its inclusion in the film. “Stay” became a hit and eventually topped the Billboard Hot 100. It also proves that not every breakup hit in the 90s was delivered with rage.

“Linger” by The Cranberries

Dolores O’Riordan’s lilting voice and its Gaelic roots became instantly recognizable in the 90s. The Cranberries had massive hits with “Zombie”, “Dreams”, and “Linger”. And in “Linger”, the residual heartbreak from a failed relationship won’t heal. O’Riordan delivers the song’s saddest lyric, “So why were you holding her hand?” almost in passing. She’s spiraling emotionally, and the near whisper makes it feel like she can barely catch her breath.

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