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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 Nerve 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.