The 25 Greatest Breakup Songs of the 1990s

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The 25 Greatest Breakup Songs of the 1990s

We recently assembled the greatest love songs of all time, but let's face it: while love has inspired some great songs, the majority of classics come from a darker place. Our rules this time were simple: a breakup song can be vengeful, dignified, devastated, or whatever else, as long as the lyrics make explicit reference to a relationship that is ending or has ended. Again, we limited it to one song per songwriter (not necessarily per band). Come back next week for the best breakup songs of the '00s, and let us know what we missed in the comments. Also, feel better. You're going to get through this, and to help with that, here's a Spotify playlist of this week's list, and here are the greatest breakup songs of the '60s, the '70s, and the '80s. — The Hooksexup Editors

25. Everclear, "The Twistinside" (1995)

I know, but they used to be good. There's not a bad song on Sparkle and Fade (even Robert Christgau liked it!), but this is one of the best, a barroom epic about the end of a suffocating relationship. It builds from a lulled beginning to an explosive, cathartic end: "I don't want to die with you, or live in the same dark room… I know the secret of your soul, and I just don't want to know." — P.S.


24. Aimee Mann, "Amateur" (1997)

Over a carnivalesque instrumental track, Mann sings about hoping against reason to find something better in a person (and by extension, their relationship) than there actually is. Articulating disappointment, but forgoing bitterness, Mann acknowledges her own blind spot: "I thought you'd be better, but I've been wrong before." — A.H.


23. Guns N' Roses, "November Rain" (1992)

It's possible that no one since Axl Rose has written a breakup song this grandiose. There's good reason for that; bombast on this scale calls for years if not decades of back-to-basics purification. But. But! There is also no human experience more grandiose, on the inside, than a breakup. Thus, when you need it, "November Rain" will serve you well. — P.S.


22. Red Hot Chili Peppers, "I Could Have Lied" (1991)

There's no slap bass. There's no rapping. There's just a beautiful guitar figure, a rare set of emotionally vulnerable lyrics from Anthony Kiedis, and not one but two guitar solos that define "wailing." Also, the song is allegedly about Sinead O'Connor, which gives this list a weird, "two people in the same room who used to date" feel. Awkward. — A.H.


21. TLC, "I Miss You So Much" (1999)

"I Miss You So Much" was lost among the hurricane of bravado that was "No Scrubs" and its follow-up empowerment anthem, "Unpretty," but it's a great slice of '90s R&B; a soft, delicate ballad that features absolutely zero attitude and a distinct paucity of condom-eyeglasses. This is a TLC that didn't really come out that much — wounded and laid bare — which makes its rare appearance that much more effective. — A.H.


20. Bell Biv DeVoe, "Poison" (1990)

Some say this old-school classic plays to a new era of AIDS consciousness — meaning that, like poison, that girl is literally deadly. I tend to think it's just about a toxic kinda woman, but what really matters is that this song stands the test of time. The scratched record and beat are as catchy now as they were then. And most importantly, this track teaches us an important life lesson: never trust a big butt and smile.  — R.K.


19. Alice in Chains, "Heaven Beside You" (1995)

Sung by Jerry Cantrell instead of Layne Staley, "Heaven Beside You" concerns the breakup of Cantrell's seven-year relationship, and it sandwiches perfectly between AIC's two primary moods: bleak and really fucking bleak. Largely acoustic, it's slightly less stomping than the rest of Alice in Chains' catalog. But the band's signature elements (CSNY-on-downers harmonies and epic guitar solos) are fully intact, making this the kind of breakup song acceptable to self-loathing metal dudes the world over. — A.H.


18. Mariah Carey, "Heartbreaker" (1999)

Not all breakup songs have to feature sadness and acoustic guitars. Sometimes, getting over a breakup can be as simple as listening to Jay-Z's incessant commands to "Bounce to this" and letting yourself get lost in Mariah Carey's sex-kitten delivery. — A.H.


17. Boyz II Men, "End of the Road" (1992)

Anyone else remember swaying slowly to this at middle-school dances? Even then, I knew this was a classic. It's a quintessential goodbye song — but can't we have just one more dance? — R.K.


16. Green Day, "When I Come Around" (1994)

Green Day's success probably had as much to do with their rhythm section as with anything else (hooks, cuteness). It's not that they're doing anything tricky, but they've got some snap, and that means Green Day just feels good to listen to. In this case, the lyrics to "When I Come Around" don't really say much about the relationship we're strutting out of, but the music sure makes us feel like strutting. — P.S.


15. Lauryn Hill, "Ex-Factor" (1998)

Preternaturally gifted as a rapper, producer, and singer, Lauryn Hill really could do it all. The Miseducation of Lauryn Hill touched on virtually every kind of pain there is, from racism to disenfranchisement to plain-and-simple heartbreak. The last reached its exquisite peak with "Ex-Factor," which Wyclef Jean has since revealed is about him. "Cry for me, cry for me, you said you'd die for me," an overdubbed choir of Hills sings accusingly at the song's climax  it's hard not to feel like you're in the crosshairs during that line. — A.H.


14. Smashing Pumpkins, "Perfect" (1998)

Our other Smashing Pumpkins nomination was more characteristic: "Soma," a dreamy, seven-minute psych-rock epic. "Perfect" falls at the opposite end of the spectrum. It's a low-key, gentle, honestly sweet farewell, wistfully anticipating a future where two lovers have become two strangers passing in the street. Always a weird experience. — P.S.


13. Fiona Apple, "Sleep to Dream" (1996)

Fiona Apple is the voice of smart women everywhere who are consistently underwhelmed by their men. "Sleep to Dream" is the best of her many, many breakup songs; they're all great, but this one is damn empowering. You can't hear it without feeling at least a little more badass, even if you aren't getting over someone. The reprise says it all: "So don't forget what I told you / Don't come around, I got my own hell to raise." Preach, Fiona, preach. — R.K.


12. Stone Temple Pilots, "Interstate Love Song" (1994)

That monster riff might not immediately scream "breakup" — to me, it screams "bitchin'" — but with lyrics like "You lied, goodbye" prefacing "Leavin' on a southern train," it's not hard to assume it's about some kind of breakup. Or heroin. Probably both, actually. Either way, it's a great song to play when triumphantly driving down the road, one arm high in the air. — A.H.


11. Ben Folds Five, "Song for the Dumped" (1997)

In one of the angriest breakup songs of the '90s, Ben Folds makes damn sure that his ex gives him back all the souvenirs she collected during their relationship. Whatever she did that warrants being called a "bitch" over and over must've been bad. Let's just hope he finally got his black t-shirt back. — J.G.


10. No Doubt, "Don't Speak" (1996)

Originally a celebration of love between Gwen Stefani and Tony Kanal, "Don't Speak" was later rewritten to reflect their breakup. Through Stefani's remorse-laden voice, it reminds of us the times we want to shrink away from the harsh truth, and choose silence over angry words. — J.G.


9. The Magnetic Fields, "All My Little Words" (1999)

Writing a song is always an act of hope — you'll get your feelings across to someone in a way that matters. You'll create or reaffirm a connection. But after a breakup, all hope is lost, and not even a craftsman as crafty as Stephin Merritt can write anything to fix it. Meaning itself is annihilated, leaving just a pile of forlorn verbiage. I wish I could write songs this good, but then, what difference would it make? — P.S.


8. Jeff Buckley, "Lover, You Should've Come Over" (1994)

Jeff Buckley's more known for his epochal cover of "Hallelujah," but "Lover, You Should've Come Over" showcases the sophistication of his own songwriting. With chords more inspired by jazz than rock and a voice that sounds decades wearier than it has any right to, "Lover" is an elegiac ode to lost love from someone who seemed to know more about losing love than any of us. — A.H.


7. Pearl Jam, "Black" (1991)

Pearl Jam were always unapologetic classicists, and everything about this song, from the delicately filigreed guitar work to the relentless stomp of the drums, trumpets classic rock's disregard for subtlety. That said, bombast is also extremely cathartic (see also "November Rain"), and by the end of the song, Eddie Vedder's pain is palpable, and universal: "I know someday you'll have a beautiful life, I know you'll be a star in someone else's sky, but why can't it be mine?" — A.H.


6. Radiohead, "High and Dry"

"High and Dry" is about compromising your integrity for someone you love. Lyrics like "kill yourself to never ever stop" remind us of how badly you're willing to make sacrifices to keep your love close to you, while Thom Yorke's teetering-on-the-verge-of-madness voice invites you to recognize your own bad choices. — J.G.


5. Weezer, "Butterfly" (1996)

Closing out a near-perfect album of guilt and angst, "Butterfly" is a devastating story about the guilt of being unable to commit. Totally exposed, Rivers Cuomo confesses to having hurt someone who didn't deserve it. He tries to figure out why he did it, but in the end, all he has are two plaintive words: "I'm sorry." — P.S.


4. Notorious B.I.G., "Friend of Mine" (1994)

This is an ode to those relationships in which both parties screw everything up royally. Biggie gives us the backstory of himself and his lady, which is rife with lies, infidelity, and smack-talkin'. Sometimes the only direction you can point your finger is at yourself. — J.G.


3. Liz Phair, "Fuck and Run" (1993)

The musical, lyrical, and spiritual opposite of "November Rain," "Fuck and Run" is wistful and blunt. A not-very-passionate relationship is dropping off, and it sounds like it's only the most recent of many. This is the lament of someone who wants something more, but is too paralyzed to reach for it. — P.S.


2. Elliott Smith, "Oh Well, Okay" (1998)

In a discography full of gorgeous, devastating breakup songs, it's hard to pick just one. (Also nominated: "Say Yes," "Waltz #2," "Miss Misery," "Between the Bars," "The Biggest Lie," "Condor Ave.," etc.) But "Oh Well, Okay" might be the best of the bunch, a sigh of resignation wedded to one of the most beautiful melodies poor Elliott Smith ever wrote. — P.S.


1. Sinead O'Connor, "Nothing Compares 2 U" (1990)

In my opinion, this is one of the few covers that blows the original out of the water. (My apologies to all the Prince fans out there.) With devastating honesty, Sinead O'Connor mourns a straying lover, while celebrating the freedom of being alone again. Life's great buffet is hers for the taking, but it's all lost its taste. — J.G.


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