20. Chris Isaak, "Wicked Game" (1989)


This song has one of the sexiest videos of all time, and that weird Elvis-aping hiccupy vocal tic is undeniably catchy. Isaak's vocal and and James Wilsey's guitar licks are live, but the rhythm tracks are loops constructed from previous takes — the way they push against each other is a little disorienting, and that gives the song a loose feel that perfectly paints a boozy night of regret. — A.H.

 

19. Janet Jackson, "Come Back to Me" (1989)


So much of Rhythm Nation is so stern and authoritative that when "Come Back to Me" drops, it's hard to believe this is our Dear Leader dropping her guard to plead with a departed lover. That juxtaposition makes it all the more effective, and all the more moving. — A.H.

 

18. Hüsker Dü, "Don't Want To Know If You Are Lonely" (1986)


With text messages and voicemail replacing the answering machine, the feeling of ignoring a call while listening to someone leave a message is gone forever. In ten years, your average post-grad will never know the feeling of listening to a 4 a.m. message come in from a recently departed boy/girlfriend. Luckily, they'll have one of the best Hüsker Dü songs to commemorate the experience. — Sean Morrow

 

17. Bob Dylan, "Most of the Time" (1989)


"Most of the Time" beautifully captures that nagging little voice inside your head that sneaks up on you at the most unexpected moments. "Don't even remember what her lips felt like on mine" — damn it, Bob, yeah, you do! — J.G.

 

16. REM, "The One I Love" (1987)


Here's a classic of the "frequently misinterpreted lyrics" genre. Michael Stipe says "The One I Love" is about "using people over and over again." In that sense, this is about not only giving up your lost love, but your own terrible habits as well. — J.G.

 

Commentarium (44 Comments)

Apr 09 12 - 12:56am
abloob

Perfect #1. I always associated Always On My Mind with the Pet Shop Boys, rather than Willie Nelson. I'm probably in the minority there.

Apr 09 12 - 11:46am
Elvis P

You should've had my version on your 70's list.

Apr 09 12 - 1:19am
Anon

I know it's a much more obvious choice than a lot of the songs on this list, but surely Alison Moyet's voice earns "Only You" a spot somewhere? Otherwise, damn great list. Looking forward to the 90s.

Apr 09 12 - 3:54am
abloob

Is it too early to predict Black #1 for the 90's list?

Apr 09 12 - 11:44am
I might be wrong

Wasn't OMD's "If You Leave" a breakup song? And wasn't it released in the '80s? That would be tops (or near the top) of my list, for sure.

Apr 12 12 - 4:50pm
Csupply

Oh man, no kidding!

Apr 09 12 - 4:53pm
RN

Two points: one, the sad part of Tracy Chapman's "Fast Car" is that it ISN'T a breakup song. She's still got the loser at the end, they've got kids, she's supporting his drinking with a crappy job, and her hopes for change are futile: "I always hoped for better, but maybe together you and me'll find it; I got no plans, I ain't goin' nowhere; take a fast car and keep on driving." The end.
Two: the best breakup song of the 80s was John Waite's "Missing You." I don't care how mainstream that was or that Waite was a one-hit wonder. As someone whose first boyfriend dumped her in 1984 at the age of 15, I declare with unimpeachable authority that "Missing You" should be, must be, and indeed is, number one.

Apr 09 12 - 5:04pm
tmp

"I'd always hoped for better
Thought maybe together you and me would find it
I got no plans I ain't going nowhere
So take your fast car and keep on driving"

Apr 10 12 - 7:46pm
RN

Who knew? Two little misheard lyrics--the "thought" and the "your"-- and I had the ending all wrong. (Now you're going to tell me that ACDC doesn't really sing "yeah, should we all die young!")

Apr 09 12 - 8:01pm
Jud

Isn't Tracy Chapman gay? Wouldn't it be her woman that she's singing to then, and not her man?

Apr 10 12 - 12:50am
Charlotte

Yes, and who cares? It's not necessarily about her. It's just a song.

Apr 09 12 - 9:16pm
Ph

The no 1 is right but where is joy division's love will tear us apart and prefab sprout's when love breaks down ?

Apr 10 12 - 6:40am
M

I'm pretty sure Joy Division snuck into the 70's list..

Apr 10 12 - 12:48pm
Ph

yeah u r right but the song was actually released in 1980

Apr 09 12 - 11:38pm
Victor

This list is very/surprisingly white. Where's all the R&B/soul? "Superstar/Until You Come Back To Me" by Luther Vandross is a serious omission (9+ minutes of heartbreak from the best soul singer of the decade). And I think Lisa Stansfield's "All Around The World" came out in 1989. Also, "The Rain" by Oran Juice Jones would have been a cool pick (if only for the spoken word kiss-off at the end).

Apr 10 12 - 7:52am
Amybelle

U2 With or Without You.

Apr 10 12 - 9:57am
Buzz

No "The Breakup Song" by the Greg Kihn Band? Easily #1 in my book.

Apr 10 12 - 2:08pm
JJ

No kidding. How is the BREAKUP song not on a list of Breakup songs?

Apr 13 12 - 4:00pm
They Don't Write 'Em

Thank you! I saw this article and of course the first thing to pop into my head was I bet the idiot writer who put this together won't even have "The Breakup Song" on this list because that would be right in line with the idiots who've been putting together these lists. And once again Nerve, you didn't let me down! Please get writers who at least have SOME knowledge of the topics for which they say they're writing about!

Apr 10 12 - 10:28am
Mary

My pick for greatest (as in heartbreaking) is "In Too Deep" by Genesis; still can't listen to that one without tearing up.

Apr 10 12 - 2:14pm
JJ

On My Own by Michael McDonald and Patti LaBelle. Simply because Michael McDonald rules.

Apr 10 12 - 3:50pm
justbroken

Romeo and Juliet. DIES. (No pun intended.) God, those lyrics.

"I can't do everything, but I'd do anything for you. I can't do anything except be in love with you."

WAH.

Apr 13 12 - 1:17am
sotrue

When I clicked on this story, I was hoping to see "Romeo and Juliet." Beautiful song ... one of the best.

Apr 10 12 - 10:08pm
hestcm01

"This Is the Way We Make a Broken Heart..." written by John Hiatt, recorded by Rosanne Cash. Should be on this list. Written from the homewrecker's point of view, with a slinky, cynical backbeat. Everything you'd expect the other woman to think.

Apr 10 12 - 10:49pm
Just Vomited on List

Read your list and just vomited on my computer.

Apr 11 12 - 11:59am
jillian

How about "Cuts like a Knife" Bryan Adams...also can't believe nothing from Robert Cray Band made the list...the guy wrote whole albums worth of infidelity, breakup and sorrow...

Apr 11 12 - 4:08pm
Spare Parts

Bruce Springsteen's "When You're Alone" or "Brilliant Disguise"

Apr 11 12 - 7:30pm
Yasmin

Very happy with this one: as soon as I saw the title, "I Know It's Over" came over my mind.

Apr 12 12 - 4:46pm
Jarvik7

Seems to me nearly a third of Husker Du's oeuvre consisted of fantastic breakup songs. Nice to see them, as well as the Replacements, represented here.

Apr 12 12 - 5:15pm
Todd Mason

"Hero Takes a Fall" The Bangles.

Apr 12 12 - 5:25pm
Undawater

Money Changes Everything

Apr 12 12 - 7:10pm
Serge

Give Me Back My man is about a shark who eats Cindy's boyfriend. She entices the shark with fish and candy. It's not about "putting out".

Apr 13 12 - 3:48am
UHF

Seriously, where is Abba's The Winner Takes It All and George Michael/Wham's Careless Whisper? They definitely deserve a spot over Janet Jackson and Paula Abdul!

Apr 13 12 - 4:16am
Sof

Where's Billy Idol's Eyes without a face?

Apr 13 12 - 11:15am
Trevor

What about The Police, "Can't Stand Losing You"?

Apr 14 12 - 12:19pm
UHF

Can't Stand Losing You came out on Outlandos d'Amour in 1978

Apr 15 12 - 10:59am
Lawrence

Roxy Music nowhere to be found???? Slave to Love??? No Police??? Wrapped Around Your Finger??? However, even though he's just making the scene, Gotye's Somebody That I Used to Know would be the most torturous song on the list.

Apr 20 12 - 11:41am
Luigi

How in the hell is, 'every rose has a thorn' not on this list? Your entire website is invalidated by this oversight, sirs.

Apr 20 12 - 11:38pm
Sarah

How can not list Yaz-- "Only You""...major heartbreak.

Apr 21 12 - 2:33am
Ian

Billy Vera and the Beaters - At This Moment

May 15 12 - 10:25pm
Josh Fitz

Are you guys too hip to include ABBA's "The Winner Takes It All", quite simply the most eloquent breakup song ever written or recorded. It may not be alt or indie, but it's undeniably moving and wrenching in much the same way all the other songs on your list are. A glaring omission.

Aug 09 12 - 6:49am
Katiel

Spending my time by Roxette. Helped me get over my asshole ex boyfriend.

Aug 30 12 - 11:11pm
MitchD

I see there is no love for John Waite's Missing You eh, shame really.

Sep 05 12 - 8:31pm
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