The 30 Best Kiss-Offs in Musical History

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Face it, we all like a good lyrical smackdown, and the art of the kiss-off line (or, indeed, entire kiss-off song) is one of the most time-honored and enduring in music. Good kiss-offs can take many forms — they can be subtle and sarcastic, or blunt and brutal, or just flat-out hilarious. Either way, there have been many, many good ones committed to tape over the years, and we’ve always had an ear for a biting turn of phrase — so we’re counting down 30 of the best after the jump. As ever, we’re open to suggestions, so let us know your favorites!

30. Ween — “Piss Up a Rope”

The pitch-perfect country satire of 12 Golden Country Greats reached its zenith with “Piss Up a Rope.” The glory of this song is that it could quite happily be a genuine country song (in the vein of similar gems like Ray Stevens’ “Get Your Tongue Out of My Mouth, I’m Kissing You Goodbye”), albeit one full of Gene ‘n’ Deen’s, um, unique brand of humor.

Key lines: “For the last six months I’ve been packing your bag/ You can wash my balls with a warm wet rag/ ‘Til my balls feel smooth, and soft like silk/ I’m sick of your mouth and your 2% milk”

29. Nancy Sinatra — “These Boots Were Made For Walking”

And that’s just what they’ll do!

Key lines: “You keep samin’ when you oughta be changin’/ What’s right is right, but you ain’t been right yet”

28. The Shangri-Las — “He Cried”

Despite the Motown production sheen, this is a surprisingly brutal piece of work, and all the more so considering it was being sung by three girls still in their teens. Of course, teenage girls can be the bitchiest people on the planet, but still, there’s something disconcertingly cold-hearted about how dispassionately the Shangri-Las recount inflicting heartbreak.

Key lines: “I knew that our romance was over and done/ But for him it had just begun”

27. Rowland S. Howard — “I Burnt Your Clothes”

The late and great Rowland S. Howard included a reworking of “He Cried” on his 1999 masterpiece Teenage Snuff Film — right before this song, which is even more vicious (as its title might suggest). It’s Howard’s utter detachment that makes this so compelling — and all the more so because of the sense that he’s just as appalled by his actions as the listener is.

Key lines: “Guess what? I don’t care/ About who, or what, or when, or where/ And heaven knows/ I burnt your clothes”

26. Iggy and the Stooges — “I’m Sick of You”

For all Iggy’s reputation as a hellraiser, there was always plenty of humor in the Stooges’ work — and it’s in full effect in this song, a gloriously truculent farewell to monogamy and responsibility.

Key lines: “I’m sick of hanging around your pad/ I’m sick of your mum, and I’m sick of your dad”

25. Rufus Wainwright — “California”

Of course, kiss-offs don’t have to be directed at people — as Rufus Wainwright proves with this song, they can be directed at entire states. And no, we can’t really imagine Rufus fitting in on Venice Beach, either.

Key lines: “California/ You’re such a wonder/ That I think I’ll stay in bed”

24. Sebadoh — “The Freed Pig”

And, of course, they can be directed at former bandmates. By the sounds of this song, being in Dinosaur Jr with the legendarily grumpy J. Mascis really wasn’t much fun for Lou Barlow, although lines like, “I tried to bury you with guilt/ I wanted to prove you wrong” suggest that he wasn’t exactly a barrel of laughs himself. Either way, this is one of the most bitter songs directed at a former colleague you’re ever likely to hear.

Key lines: “With no sick people tugging on your sleeve/ Your big head has more room to grow/ A glory I will never know”

23. REM — “The One I Love”

We touched on this a while back in our feature on the most misunderstood songs in music. You can certainly appreciate Michael Stipe’s bewilderment at seeing people wave lighters and make out to what’s almost certainly the nastiest song he ever wrote — a callous kiss-off to a former lover, in which he describes the scorned party as “a simple prop to occupy my time.”

Key line: “Another prop has occupied my time”

22. The Delgados — “If This Is a Plan”

If you’ve ever carried a torch for someone, you’ll know how liberating finally extinguishing said torch can be. This song recounts finally deciding that lusting after an old flame “isn’t worth it,” especially since he/she isn’t leaving her significant other any time soon.

Key line: “You look older/ You look harder and colder/ Is this what ten years with a dickhead can bring?”

21. Arab Strap — “The Girl I Loved Before I Fucked”

While we’re on Scottish misanthropes, we couldn’t possibly forget Arab Strap, the band whose name is essentially synonymous with sordid, bruised vignettes about the night before and the morning after. As with all the band’s lyrics, this is ambivalent about its subject, and about the whole idea of love — it’s curiously romantic in its own way, but also suitably biting.

Key line: “You’re the girl I loved before I fucked and that’s so rare/ So I’ll help you leave your home while you decide if you still care”

20. mclusky — “Collagen Rock”

In which Andy Falkous dismisses his contemporaries by comparing them to vapid fashion models. Like all Falkous’s best lyrics, it’s surreal, angry, more than a little bizarre, and entirely hilarious.

Key line: “One of those bands got paid, I heard/ One of those bands got fake! Tits! Yeah!”

19. Lily Allen — “Not Big”

The title says it all, really — but if it wasn’t enough of a hint, then the chorus of this song makes it pretty clear that Allen’s talking about her lover’s manhood. And then there’s the verses, which note that “you never made me come/ In the year and a half we spent together,” and also that she’s planning to “work my way through your friends.” Ouch.

Key lines: “You’re not big, you’re not clever/ You ain’t a big brother/ Not big, whatsoever

18. Violent Femmes — “Ugly”

Yes, of course the Femmes were going to feature on this list — shit, they even wrote a song called “Kiss Off.” But while we love that track, we reckon their best and bitterest lines come in this song, a gloriously bratty denunciation of a former paramour who, as Gordon Gano tells it, was no oil painting.

Key lines: “Engaged in some sexual acts/ But I’m just gonna have to tell you the facts/ There’s something I figured out about you… You’re ugly! Ugly! Ugly! Ugly!”

17. Elvis Costello — “I Hope You’re Happy Now”

We wouldn’t want to get on the wrong side of Elvis Costello, frankly. This song breaks out the nastiest thing you can say to a former lover — “I never loved you anyhow” — and also manages to use the phrase “pork sword,” which is inherently hilarious whichever way you look at it.

Key lines: “He’s acting innocent and proud still you know what he’s after/ Like a matador with his pork sword, while we all die of laughter”

16. Brian Eno — “Dead Finks Don’t Talk”

In which Eno snipes at Bryan Ferry in a manner that’s both amusing and biting. Roxy Music wasn’t big enough for two Brian/Bryans, clearly.

Key line: “To be a zombie all the time/ Takes such dedication”

15. Bonnie “Prince” Billy — “Break of Day”

There’s something more than a little unsavory about Will Oldham’s alter ego, and never more so than in this song, which finds him lying awake in bed with his lover, waiting until the morning — when he plans to dump her.

Key line: “Dawn is mine and I will share it/ With whatever bird will wear it/ On her body, bare and pink/ Now what do you think of break of day?”

14. L7 — “Shitlist”

Yes. The best song ever to put on the stereo when someone has really, really given you the shits.

Key line: “You’ve made my/ SHITLIST!”

13. The Rapture — “No Sex for Ben”

Now that The Rapture are making underwhelming and weirdly Christian records, it’s easy to forget that they recorded this glorious broadside (apparently directed at DJing contemporary Ben Rymer).

Key line: “Ben Rama/ Big time lover/ Trying to snatch the kitty off his girlfriend’s mother/ No sex for Ben!”

12. Amy Winehouse — “Fuck Me Pumps”

One of the saddest things about Amy Winehouse’s slow decline and tragic demise is that everyone seems to have forgotten how witty and hilarious she was in her early days. “Fuck Me Pumps” remains her funniest song, a supremely bitchy and giggle-inducingly accurate evisceration of vapid scenester groupie types.

Key line: “With your big empty purse/ Every week it gets worse/ At least your breasts cost more than hers”

11. Elastica — “Line Up”

In the same vein but a decade earlier, Justine Frischmann spent the first track on Elastica’s self-titled debut administering a sound lyrical thrashing to the female hangers-on of the Britpop scene. Extra points for Justin Welch’s vomit sounds in the intro.

Key line: “You can’t see the wood for the trees/ On your knees”

10. Oran “Juice” Jones — “The Rain”

The quintessential iron fist in a velvet glove — underneath the smooth R&B styling of “The Rain” is all the fury of a betrayed boyfriend, a fury that eventually manifests in the song’s extended outro, where Jones confesses wanting to shoot both his soon-to-be-former girlfriend and her lover (“But I didn’t want to mess up this $3700 lynx coat”), proclaims “You don’t mess with the Juice!,” and eventually turfs her out onto the street.

Key line: “Dismissed!”

9. Alanis Morrissette — “You Oughta Know”

Hell hath no fury, etc etc.

Key line: “And are you thinking of me when you fuck her?”

8. Fleetwood Mac — “Go Your Own Way”

Rumours is the most legendarily dysfunctional record in rock ‘n’ roll, the sound of a band shagging furtively behind each other’s backs and snorting waaaaaay too much coke while doing so. The genius of this line lies in the fact that not only did Lindsey Buckingham write a blunt dismissal of Stevie Nicks, he then proceeded to make her sing it.

Key line: “You can go your own way/ You can call it another lonely day”

7. Pulp — “Pencil Skirt”

As you’d expect from one of finest lyricists in music, Jarvis Cocker has been responsible for his fair share of acerbic dismissals (see the denouement of “This Is Hardcore,” “Pink Glove,” and, of course, all of “Common People”). We’ve always been partial to to “Pencil Skirt,” though, which isn’t so much a kiss-off to a lover as it is to the whole idea of love.

Key line: “Now you can tell some lies about the good times that you’ve had/ But I’ve kissed your mother twice/ And I’m working on your dad”

6. Bob Dylan — “Positively 4th Street”

Dylan also has plenty of these to choose from — you could take your pick from most of “Like a Rolling Stone,” for a start — but we’ve always liked this lyrical beatdown of an unnamed Greenwich Village antagonist. The best thing about this song is that Dylan never specified who it was about — which led to plenty of his contemporaries assuming it was about them. Talk about killing multiple birds with a single well-aimed stone.

Key line: “I wish that for just one time you could stand inside my shoes/ You’d know what a drag it is/ To see you”

5. Grace Jones — “Private Life”

Not only is Grace Jones genuinely terrifying, she does a fine line in lyrical put-downs — and none better than this trituration of a hapless paramour. Curiously, this was written by Danny Elfman. Who’d have thought he had it in him?

Key line: “Your marriage is a tragedy/ But it’s not my concern”

4. The Smiths — “Frankly, Mr Shankly”

Morrissey is another artist who’s made a living out of pithy, razor-sharp kiss-offs, but our favorite is one that eschews subtlety in its denunciation of a former employer. The denouement to this song works because of its context — the song starts out obliquely enough, but becomes more and more amusingly direct as Morrissey audibly loses patience with its subject.

Key line: “Frankly, Mr Shankly, since you asked/ You are a flatulent pain in the ass”

3. Cee-Lo Green — “Fuck You”

Beneath the oh-so-hummable melody to what in our opinion is the finest pop song of 2010 lies a very genuine bitterness, and a great deal of glee in finally being in a position to send a whole lot of triumphant success back in the direction of a girl who chucked him when he was broke.

Key line: The entire song, basically. But especially “Although there’s pain in my chest/ I still wish you the best/ With a ‘fuck you’!”

2. John Lennon — “How Do You Sleep?”

Crikey, Lennon really didn’t think a whole lot of McCartney, did he?

Key line: “The only thing you done was yesterday/ And since you’re gone you’re just another day”

1. Marianne Faithfull — “Why D’ya Do It?”

And at #1, behold: the one song that basically makes us want to hide under the table every time it comes on the stereo. It’s not often we feel sorry for Mick Jagger, but if it had been us on the other end of this tirade, it’d probably have taken years to recover.

Key line: “Why’d ya do it?, she said/ When you know it makes me sore/ She had cobwebs up her fanny/ And I believe in giving to the poor”