The five best movie breakups

There’s only one thing worse than spending Valentine’s Day without someone to love; it’s forgetting to celebrate the one you love, and spending the next few days reflecting on why you got dumped. While you’re at it, watch these movies and weep.


City Lights (1931)

  • Is it true that even in love, no good deed goes unpunished? The Little Tramp does everything he can to help the flower girl and win her heart, most of it pretty hilarious. Does he succeed? The last scene is open to interpretation, but I find it the saddest thing that Charlie Chaplin, or anyone, has ever put on the screen.


Casablanca (1942)

  • Just a hill of beans? Generations of heartbroken fans think not. But you can take some consolation in the fact that Humphrey Bogart’s Rick did manage to hook up with Claude Rains’s Captain Renault on the rebound.

A Streetcar Named Desire (1951)

  • “Never going back there,” says Stella (Kim Hunter), baby in her arms, as Stanley (Marlon Brando) bellows her name off-screen. “Never.” Well, it’s about time. He may be hot, but he’s a lout, and you can only hope that she sticks to her decision not to return to an abusive domestic situation.

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Play Misty for Me (1971)

  • Clint Eastwood’s directorial debut, in which he also starred as a disc jockey stalked by a fan, seemed at the time to confirm him as a macho pig. Throwing someone off a cliff will do that. But a closer reading reveals a subversive, feminist subtext. Anyway, much better than the 1987 rip-off, “Fatal Attraction.”


Brokeback Mountain (2005)

  • “I wish I knew how to quit you,” entered the movie quotation pantheon after it was muttered in this classy, groundbreaking tearjerker about the tragic love between two cowpokes in Wyoming in 1963. Well, they finally figured out how to quit each other, and now we still cry our eyes out over that darned shirt.

  • COMING UP: There will always be another film about that one last heist, that final fatal assignment. Which is your favorite? And looking ahead to March 2, “Son of God” (opens Feb. 28) is the latest in a long line of movies about Jesus Christ. Which versions are worthy of the subject? Cast your votes at

Peter Keough can be reached at
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