The five sassiest breakup songs of all time

Katie and Tom, Katy and Russell -- everybody's breaking up these days, it seems. Hell, even Adam Levine traded in one Victoria's Secret model for another. Break ups aren't just relegated to the super couples or the superstars, obviously. Everybody's been on the receiving end of being dumped -- or done the dumping, as the case may be. It's no wonder then that Deerhoof decided to title its forthcoming album, Breakup Song. With this in mind, here are five of the sassiest breakup songs of all time. What are yours?

5. Rilo Kiley: "Breakin' Up"

"Here's to all the pretty girls you're gonna meet," sings a confident and subtly vindictive Jenny Lewis on this upbeat single. While the massive canon of breakup songs by Morrissey, Beck and Patsy Cline will often deal in apologetic self-loathing, this toe-tapping number carries an unmistakable air of celebration, particularly the disco-boogie breakdown where Lewis repeats the line, "ooh, yeah, feels good to be free," with declarative glee. Never did someone sound so happy making someone so sad.

4. Carly Simon: "You're So Vain"

Whether about Mick Jagger, Warren Betaty or David Bowie (who have all been suspected sources of inspiration), "You're So Vain" remains a universal slap in the face of an ex-lover with an inflated self image. Ever since the single was released, fans and curiosity seekers have been desperate to know the identity of the man in the apricot ascot, but Simon has remained silent, only releasing tiny clues here and there. The overwhelming pressure for her to reveal the Narcissus-like subject of the song only speaks to how deep a sting these lyrics cut.



Sponsor Content

Newsletters

All-access pass to the top stories, events and offers around town.

  • Top Stories
    Send:

Newsletters

All-access pass to top stories, events and offers around town.

Sign Up >

No Thanks!

Remind Me Later >