Top 10 Break-Up Songs Of All Time

NOTE: Videos have been updated (as of o5/o1/09) after some of the originals were no longer available.

You know them. You love them. Not in a "wow, this is an awesome song" kind of way, but more in a "wow, this song makes me feel awful, and right now that's perfect" kind of way. When your heart has been broken, their maudlin melodies, schmaltzy lyrics, and often overwrought performances are somehow just right.

One thing you'll quickly notice about this list is that it's based on songs from back when I was getting dumped, which was most of the eighties ... and the first part of the nineties. So you kids looking for your James Blunts and Jeff Buckleys are out of luck.

I got the idea for this list after listening to "Break-Up" on This American Life, and in particular the part of the show featuring writer Starlee Kine and her much more entertaining take on break-up songs, including her effort to write her own. I highly recommend listening to it, which you can at the link above as long as your plug-ins work better than mine seem to be.

Back to the whole "maudlin/overwrought" thing. There are limits. You'll find no Celine Dion or Michael Bolton here. And yes Whitney, I hear you wailing away back there. But no matter how many syllables you can get out of the "I" in "I Will Always Love You," you ain't gonna make my list.

I also think the best break-up songs are primarily "pop" songs. For instance, I'm a big fan of "Haunted When The Minutes Drag" by Love and Rockets, but I wouldn't say it's a classic break-up song.

You are free of course to disagree with any or all of these opinions. You'll just be wrong. Now grab your hanky and your memories and away we go ...

10. All Out Of Love - Air Supply (1980)

Boohooiest Lyrics:
There's no easy way, it gets harder each day
Please love me or I'll be gone, I'll be gone ...

Air Supply's entire catalog seems filled with very weepy songs. Maybe there's a lot more heartache down under than I remember from the Crocodile Dundee movies. I recall from another Australian band's songs of the same era that the women glow and the men plunder, so there does seem ample opportunity for romance and conflict.

Give it a listen (and a look) here, since the persnickety poster refuses to let me embed the video.


9. Hard Habit To Break - Chicago (1984)

Boohooiest Lyrics:
You dont know what ya got until its gone
And I found out just a little too late.

Chicago and lead singer Peter Cetera also had quite a few tearjerkers. Like who can forget "I Wasn't the One (Who Said Goodbye)," Pete's duet with Agnetha Faltskog (better known as the blond one from ABBA)? Still, I think this one tops them all.

*NOTE: This was one of the videos on this list the knuckleheads at Warner Brothers music forced YouTube to take down. So this is a poor quality live version. It was the only one I could find that still have Peter Cetera singing (since that's the real "Chicago").




8. Love Theme From St. Elmo's Fire/For Just A Moment - David Foster (1985)

Boohooiest Lyrics:
Time goes on
People touch and then they're gone
And you and I
Will never love again
Like we did then ...

"What? A love theme?" you ask, quite perplexed. And yes, on the surface it does seem an odd choice. But if you've ever heard the somewhat-rare vocal version with lyrics like those above, you'll get the full bittersweet vibe only hinted at by the wailing saxophone in the more common instrumental version. As a vaguely interesting side note, many years after first hearing the vocal version, I actually met the male vocalist, Donny Gerrard, who was working on some jingles for the ad agency I was working at.

Sadly, due to some pesky copyright issues, the original video I had up here was taken down. So now you'll have to settle for hearing the instrumental version over some of the final scenes of the movie. The song kicks in about 4:40.




7. Love Hurts - Nazareth (1975)

Boohooiest Lyrics:
I know it isn't true
Love is just a lie made to make you blue ...

This song was already "classic rock" by the time I could start identifying with it, but even though I'm generally not a fan of the rock ballad (particularly the dreaded "power ballad"), the purity of this one gets it on the list: "Love hurts. Love scars. Love wounds, and mars." Ouch.

While the Nazareth version is generally thought of as the "definitive" version (with Roy Orbison a strong second), it was first recorded by the Everley brothers back in 1960. Since then, everyone from Joan Jett and Cher to Pat Boone and Rod Stewart have taken a shot at it.



6. Pictures of You - The Cure (1989)

Boohooiest Lyrics:
There was nothing in the world that I ever wanted more
than to feel you deep in my heart ...

I suppose this technically strays outside the "pop" category that I had said was a requirement earlier. But Robert Smith was just made to sing break-up songs. Not just the voice, but the added anguish that comes into play when his mascara starts to run. Even on "Friday I'm In Love" he sounds more at home during the song's mid-week "Tuesday's grey and Wednesday too."




5. Every Breath You Take - The Police (1983)

Boohooiest Lyrics:
I look around, but it's you I can't replace
I feel so cold, and I long for your embrace
I keep crying baby, baby please ...

There's more than a bit of obsession in this song, something that's often a common component of many breakups (not mine, of course, despite what those restraining orders may imply). Sting says of the song: "I didn't realise at the time how sinister it is. I think I was thinking of "Big Brother," surveillance and control." But he wrote it during the breakup of his first marriage, so it definitely qualifies. It also has this cool black and white video, which definitely fits the break-up mood. At least the black part.

Thanks to the wishes of the Universal Music Group, I can't embed the video, but at least they'll let me link to it.


4. All I Want Is You - U2 (1989)

Boohooiest Lyrics:
All the promises we break
From the cradle to the grave
When all I want is you ...

Really a tossup for me between this song and "With Or Without You." "Who's Gonna Ride Your Wild Horses" and "One" are also legitimate U2-created contenders. I suppose you could make the argument that this song is more about unrequited love than a break-up, especially if you watch the Fellini-esque video here (Again with the "Embedding Disabled." Grrr).

On a side note, this song actually made its highest chart appearance in 1994, when it was re-released as a single after appearing on the soundtrack for "Reality Bites." Which was really the nineties version of the aforementioned St. Elmo's Fire. But with Stiller/Ryder/Hawke/Zellweger instead of Lowe/Moore/Estevez/Sheedy. And as a side note to this side note, in my opinion, both are inferior to 1992's "Singles" in the beautiful twenty-somethings in-and-out-of-love genre.

3. Nothing Compares 2 U - Sinead O'Connor (1990)

Boohooiest Lyrics:
Nothing can stop these lonely tears from falling
Tell me baby, where did I go wrong?

As you can tell by the pre-text messaging spelling of the title, this song was written by His Royal Purple Lowness, Prince. In fact, he originally had it recorded by a funk band called "The Family" in 1985. But Sinead made it heartbreakingly her own–and a huge hit–five years later. In fact this year VH1 ranked it #1 on their "Final Countdown - Top 50 Heartbreakers."

In this particular video, Sinead's close-up loses some of its power due to Spanish subtitles, but this is the only version I could find with the original audio. Apparently there's some pesky Prince-inspired copyright issue.




2. I Can't Make You Love Me - Bonnie Raitt (1991)

Boohooiest Lyrics:
Here in the dark, in these lonely hours
I will lay down my heart and I'll feel the power
But you won't, no you won't
'Cause I can't make you love me, if you don't ...

When I looked at lists of break-up songs that other people had composed (there's nothing new under the sun, and certainly not on the Internet), there wasn't a lot of agreement. But this song appeared on the most lists by far.

Mike Reid, who wrote the song along with Allen Shamblin, said that he was inspired to write it after reading about a man who was arrested for drunkenly shooting at his girlfriend's car. Asked if he'd learned anything by the judge, the man replied: "I learned, Your Honor, that you can't make a woman love you if she don't." And by the way, that man was not me. As far as you know.

No doubt this song came to mind when Bonnie was divorcing Danny Noonan. Here's a video of her performing it since the original video is one of the few that don't appear to be on YouTube.



1. Against All Odds (Take A Look At Me Now) - Phil Collins (1984)

Boohooiest Lyrics:
I wish I could just make you turn around,
turn around and see me cry
There's so much I need to say to you,
so many reasons why
You're the only one who really knew me at all ...

This actually makes the second list of mine that Phil Collins has topped, as readers of my Top Miami Vice Guest Stars: Musicians post will no doubt recall.

I've always thought of this as the ultimate break-up song, something that received independent confirmation in the "This American Life" story mentioned above. Starlee Kine actually interviewed Phil, and he talked about how he wrote this song as his first marriage was crashing and burning. He said that he really thought that if his wife heard this song, she'd come back to him (she didn't). And often that's another way that break-up songs make us feel: like if our ex could just hear the song; if they could just know the way we really feel, everything would be okay. Of course, as in Phil's case, that almost never happens, no matter how many times we stand outside our ex's window holding a boom box over our heads (okay, that was "In Your Eyes," not really a break-up song, but still). And you know what? Even if it takes a few months, or even a few years, we eventually learn that we're okay–and usually better off–without them.

Anyway, with my Dr. Phil moment over, I leave you with the song. Unfortunately, once again Warner Music Group has decided to deny you the original music video. And so you'll have to make due with a heartfelt live performance by Phil. Enjoy.