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.


Tags Breakups

Commentarium (59 Comments)

Apr 16 12 - 12:13am

If Aimee Mann does not pull in the top ten with any one of a zillion devastating songs for the 2000s, there will be no end to my wrath.

Apr 16 12 - 12:38am

Really? No Alanis?? "You Oughta Know" pretty much summed up how 17 year-old me felt after getting dumped over email.

Apr 16 12 - 2:06am

Oh for real, excellent call there. How did this get left out? It's still scathing and great.

Apr 16 12 - 8:50am
Alex Heigl

I think our research will bear us out.

Apr 16 12 - 2:01pm

You have Bell Biv Devoe in there.

Apr 16 12 - 6:51pm

Another vote for You Oughta Know. Sorry, your list is wrong.

Apr 16 12 - 8:02pm

You oughta know should be here. helps a LOT after breakups.

Apr 17 12 - 3:16am

Now I have memories of sitting on my high school floor, with my Walkman on, blasting that song as my "ex" walked by (I say "ex" because I was 14, we dated for 2 weeks, and I never saw him once outside of school)/ I didn't even know what going down in a theater meant. I just knew she was angry, like me.

Apr 20 12 - 3:21pm

You Oughta Know!!! And also "How's it Gonna Be" by Third Eye Blind!

Apr 22 12 - 1:42pm
Jilly Jo

What the fuck does "Our research will bear us out" even mean? If you're going to respond to readers, do them the common courtesy of taking them seriously rather than turning their very real argument into the setup for a douchey punchline.

Apr 16 12 - 2:05am

Ahh Jeff Buckley... He kind of looks like Christian Slater on that cover.

Apr 17 12 - 2:52am

I meant Ethan Hawke there.

Apr 16 12 - 5:49am
Not Noel Gallagher

Where is don't look back in anger? surely it would be near the top of the 90's!!

Apr 16 12 - 6:57am

the opening riff of "Fuck and Run", then: "I woke up, alarmed...."

I used to perform this at open mic nights with my boyfriend. It blew my mind. That whole album is just angry.

Apr 16 12 - 2:28pm

I love Liz Phair and know that album like the back of my hand. After 9 zillion listens, I kind of feel she wasn't angry so much as frustrated and misunderstood. She is really funny on her videos - look up the 120 minutes video where she and her band sing "Cinco de Mayo". Without her, no Best Coast for sure!

Now, angry...look up L7 or Hole and then move straight into the naughts with the hyper-testosteroned douchebags w/ goatees and backwards baseball caps. THAT is angry.

Apr 16 12 - 9:03am

Listening to "Lover, you should have come over" after a break up has the distinct sensation of trying to swallow a hot rock.

Apr 16 12 - 9:36am
Spare Parts

I spent the 90's being ten to twenty years old and all of my breakups in that time were inevitably accompanied by K-ci and Jo-Jo's covers of "Lately" and "If You Think You're Lonely Now." At least put some Jodeci on this list. "Cry For You"?

Apr 16 12 - 11:38pm

I'll cosign that. Something from Mary J. Blige's My Life album would've worked too -- maybe her cover of "I'm Going Down."

Apr 16 12 - 9:56am
90s kid

Ugh. I was disappointed to see No Doubt on this list, and even more so to see it rated so highly. "Don't Speak" was the number one reason I changed the radio station during my high school years. The song is gratingly annoying, and even my angsty teenage self thought the lyrics were lame.
This list is just so "meh." Was this really the best of what the 90s had to offer us?

Apr 16 12 - 10:59am

I've just realized that the majority of songs on Buckley's "Grace" are about break-ups, loss of love or the palpable absence of someone who should've been closer. "Last Goodbye" is, I think, Buckley's finest moment. An insanely catchy riff, bright sounds mixed with melancholy and beauty throughout, plus a vaguely Indian string section interlude

Apr 16 12 - 12:21pm

KC & JoJo "Crazy"?

On the other hand, thank you! I added many of these songs on Spotify :)

Apr 16 12 - 12:41pm
Esteban H

Oh man. The guitar solos on "I Could Have Lied," always give me goosebumps.

Apr 16 12 - 12:54pm

Not including "You Oughta Know" feels like a crime here, especially since she was raging against Dave Collier, aka Uncle Joey. Also, I would've chosen Weezer's "Undone (The Sweater Song)" over "Butterfly." Everyone knows The Blue Album is the best.

Apr 16 12 - 1:33pm

Gotta be the third person to mention the glaring omission of "You Oughta Know." Every woman I knew in the 90s who broke up with a boyfriend (myself included) felt like that song was written specifically for them & their exact situation during the overwrought emotional post-breakup phase!

(And does anybody else find comparing Jeff Buckley to Chrisian Slater, even look-wise, as sacrilege as I do??)

Apr 16 12 - 1:50pm

Brand New Love ..Sebadoh.

Apr 16 12 - 4:05pm

On Fire was playing in the background when my hs ex broke up with me and i cant help associate that one with heartache...even if its completely unrelated...still love Sebadoh :D

Apr 16 12 - 2:09pm

"Things Change" Dwight Yoakam

Apr 16 12 - 2:22pm

I feel like the 90s are really poorly represented in this list. There are a *lot* of more influential tunes such as the afore-commented-upon Alanis Morissette Track, the Liz Phair track (though Divorce Song is more of a breakup song than "Fuck and Run) missing. Like Portishead's "Glory Box" or "Sour Times"; PJ Harvey's "Rid of Me" or "Me-Jane"; Pulp's "Razzamatazz";

And why was "Lover, You Should've Come Over" named instead of "Last Goodbye" which is stunning and the very definition of a break-up song? (And Kelli G, I feel ya! I totally think Christian Slater and Jeff Buckley are completely different looking dudes. Not even close.)

Finally, there are a TON of hip hop tracks missing...I feel like the 90s was a golden era for hip hop. I'm at work or I'd be listing those.

The author did his/her best but man...

Apr 16 12 - 2:26pm

worst list ever... not a fan of it, but 'you outta know' shouldve been #1... Nothing compared to you was released in 90 and it was written before that...

Apr 16 12 - 3:29pm

Oh my god. How do you not put Bonnie Raitts "I can't make you love me" on here? How IN THE HELL?I don't even give a shit about Bonnie Raitt, BUT HOW????

Apr 16 12 - 6:36pm

totally agreed. that song is so incredibly beautiful, and only Bonnie can sing it right. So essential. I also agree with all the people who mentioned Alanis! That whole album has a bunch of great break up songs.

Apr 19 12 - 10:54pm

When I read the 1980's version of the breakup song list recently, I was absolutely certain that 1991's "I Can't Make You Love Me" by Bonnie Raitt would be in the Top 5 of this list, if not #1.
Its brilliantly simple elegant lyrics, hauntingly beautiful melody,
and Raitt's wonderful raspy voice -- full of pain and hopelessness --
combine perfectly to express the essence of unrequited love.
A timeless classic for jilted lovers of all ages.

Its absence here is a full-on Nerve list travesty!

Apr 20 12 - 11:01am

MThomas - I felt the same way! I thought "I Can't Make You Love Me" would definitely be on the '90s list too.

Apr 23 12 - 11:04pm

I said it. You guys said it better. Would LOVE a response from the editors...

Apr 16 12 - 9:53pm

...for some reason, Pantera's "Cemetary Gates" always did it for me.

Apr 16 12 - 9:58pm
Annan Amos

No "Tornado of Souls" by Megadeth? Weak sauce! That song has one of the greatest guitar solos ever recorded. Harumph!

Apr 16 12 - 10:36pm

Would you believe me if I said I lobbied for it? That whole album is incredible.

Apr 17 12 - 10:06am
Alex Heigl

He actually did. Vehemently.

Apr 26 12 - 12:23am
Annan Amos

I would believe it, and it most definitely is. I caught one of shows on the "Rust in Peace" 25th Anniversary Tour - got to see them play the whole album. It was legen - wait for it...hope you aren't lactose intolerant because the last word is - dary.
And the rest of you should have bloody well listened!

Apr 16 12 - 10:40pm

"Cinco de Mayo" is on Whip Smart, which is an album that definitely comes from a happier place. "Fuck and Run" is from Exile in Guyville, which also has "Divorce Song" and "Flower". It also has my favorite song of hers, "Stratford on Guy". Exile might not be as angry as I initially stated, but it's definitely an emotionally harder album.

Apr 16 12 - 11:43pm

Richard Thompson is the master of the breakup song. Might I direct your attention to his record "Mirror Blue," which contains no less than 5 classics of the genre: "The Way That It Shows," "I Ride in Your Slipstream," "Beeswing," "Mascara Tears," and "Taking My Business Elsewhere." Spotify ' won't be disappointed.

Apr 17 12 - 2:45am

Man, Good shout. 'Lover You Should've Come Over' is definitely my favourite track from Grace. Some truly wonderful lyrics in there, such as: "Too deaf, dumb and blind to see, the damage I've done." and then of course: "She's the tear that hangs inside my soul forever". Buckley's vocals are wistful but somehow optimistic nonetheless: "It's not too late". It's a song which hasn't abandoned hope quite yet.

Apr 17 12 - 11:55am

I, for one, applaud the decision to willfully ignore "You Oughta Know." That song is fucking awful. What a terrible decade.

Apr 22 12 - 7:19pm

I hated that song immediately, which was a sure sign that it would succed. Disarm by Smashing Pumpkins was another turd turned hit that drove me nuts with its lameness. Kudos to Nerve for leaving out the Alanis rant and that song by the shittiest band of the 90's, Oasis. Their music will be raping your ears as it plays out of a penis shaped radio on the elevator to hell.

Apr 17 12 - 5:44pm

So Cruel, Achtung Baby, U2

"we've crossed the line
From crush to over.........
I'm only hanging on
To watch you go down

Apr 17 12 - 6:19pm

^ I love that song and think it's severely rated in U2's discography. Perfect embodiment of a breakup

Apr 18 12 - 1:10am
Unbreak My Heart

Where's Toni Braxton?

Apr 19 12 - 8:06pm

Playing on an endless loop in that airless office I temped in through the winter of 1994. That's where. (Shudder.)

Apr 19 12 - 8:10pm

Or not, now that Wikipedia tells me it wasn't released until 96. Go figure.

Apr 20 12 - 2:23am

I'm not saying I love the song, but you have to admit it is one of the most ubiquitous breakup songs of the 90s, as evidenced by your shudder-inducing memories. At least she could sing.

Apr 18 12 - 5:55pm

I agree with the very first commenter. I love that Aimee Mann is on this list. She is overlooked way too often.

Apr 19 12 - 9:21am

Good list, but I would have added the meanest, most bitter break-up song ever: Ballad in Plain D by Bob Dylan. No list is complete without this one.

Apr 19 12 - 12:08pm

Afghan Whigs-Let Me Lie to You

Apr 19 12 - 9:10pm

Why would you even bother to make this list without "Ciao" by Lush with Jarvis Cocker?

May 09 12 - 8:10pm

How can you leave out "Breakfast at Tiffany's" by Deep Blue Something?

Jul 01 12 - 4:13am

Ugh. I had happily forgotten about that song until now. It's god fucking awful, that's why it was left off the list.

Jul 17 12 - 11:01am

For me, it was You Oughta Know and Shakira's Si Te Vas - which is a great breakup song!

Aug 30 12 - 2:59am

Sinead O'Connor's amazing delivery of "Nothing Compares 2 U" was inspired by the loss of her mother. Words are words however and be interpreted as such, but I always felt the song gave something more than the original because of the source of anguish.

Sep 05 12 - 8:29pm

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