25 best movie break-ups

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When your heart’s broken, it’s practically doctor’s orders for a big old bandage of clichés to be wrapped around it in the form of pajamas, ice-cream and a brilliant film. We’ve selected the 25 best, most brutal break-ups in movies to help put your pain in a little perspective.

Words: Tamsin Crimmens

  • (500) Days of Summer (2009)

    A typically kooky Zooey Deschanel casts a spell on Joseph Gordon-Levitt which he struggles to break as their romance falls apart. As the voiceover warns us at the beginning, this indie flick is most certainly “not a love story”.

  • Gone with the Wind (1939)

    Probably the most famous break-up line ever uttered, Rhett Butler responds to a weeping Scarlett OHara’s declarations of love with the immortal words, "Frankly, my dear, I don't give a damn" in this epic historical romance starring Vivien Leigh and Clark Cable.

  • High Fidelity (2000)

    Chronicling his top five most memorable breakups, John Cusack is a moody yet ever-so-sexy record shop owner in this adaptation of Nick Hornby’s novel. His reminiscences of being brutally dumped, including by a fabulously self-involved Catherine Zeta-Jones, are also set to a brilliant soundtrack - as every break-up should be.

  • The Break-Up (2006)

    The sight of a quietly weeping Jennifer Aniston as the realization dawns her relationship with funny-man Vince Vaughn really is over, is a poignant moment in this not-so-romantic comedy that captures how messy adult breakups can be, especially when there’s the tricky issue of joint home-ownership to contend with.

  • Eternal Sunshine of the Spotless Mind (2004)

    If you’ve ever had your heart broken you’ll know that previously happy memories of days gone by can turn into torturous obsessions. Kate Winslet and Jim Carrey star in this dreamy tale of what it would be like if you really could delete those painful memories from your brain’s hard drive.

  • Closer (2004)

    If everyone in this film wasn’t so beautiful to gaze upon we might not be able to bear watching it as hearts are trampled in vicious fashion. An adaptation of Patrick Marber’s Tony-nominated play, there’s Dawson’s Creek style articulacy aplenty as Natalie Portman, Jude Law, Julia Roberts and Clive Owen tear each other’s lives apart. No Natalie, sometimes love isn’t enough.

  • Legally Blonde (2001)

    The sweetest revenge is showing your ex how utterly brilliant you are without them. Reece Witherspoon stars as the seemingly ditzy Elle Woods who triumphs at Harvard law school after being dumped by her feeble boyfriend.

  • Annie Hall (1977)

    If you’ve ever struggled to find the words to end a failing relationship, take a tip from Woody Allen when he says to girlfriend Diane Keaton, “A relationship, I think, is like a shark, it has to constantly move forward or it dies. And I think what we got on our hands is a dead shark.” Job done.

  • Blue Valentine (2010)

    Ryan Gosling and Michelle Williams famously went all method by living together to prepare for their roles as a working-class couple. Claustrophobic, disarming and emotionally powerful, the film chronicles their relationship from adorable beginnings to devastating end - not one to watch in fresh break-up hell.

  • Casablanca (1942)

    In one of Hollywood’s most famous closing scenes, Humphrey Bogart tells love-of-his-life Ingrid Bergman to get on the plane to Lisbon with her husband saying she would regret it if she stayed, "Maybe not today, maybe not tomorrow, but soon and for the rest of your life."

  • Broken Flowers (2005)

    It’s an all-star cast in this film where Bill Murray gets dumped by Julie Delphy before revisiting former love interests played by Sharon Stone, Frances Conroy, Tilda Swinton, and Jessica Lange in hopes of finding a clue to the mystery of whether he’s fathered a 19-year-old son.

  • Forgetting Sarah Marshall (2008)

    Think back to the last time you were dumped. Painful wasn’t it? Now imaging the same scenario but you’re in your not-so-celebratory birthday suit. That’s what happens to Jason Segel when he’s jilted for outrageously oversexed rock star Russell Brand in this Judd-Apatow produced comedy.

  • The War of the Roses (1989)

    There aren’t many on-screen couplings that fizzle with as much chemistry as Michael Douglas and Kathleen Turner. Unfortunately their passion turns to hate as husband and wife plot to kill each when their divorce spins into full-on warfare.

  • When Harry Met Sally (1989)

    Mutual heartbreak brings one of cinema’s best couples together in Nora Ephron’s classic relationship tale. Meg Ryan and Billy Crystal become reluctant friends who, after helping each other through multiple breakups, eventually realise they’re meant for each other.

  • Kramer vs Kramer (1979)

    Both Dustin Hoffman and Meryl Streep won Oscars for their gut-wrenching portrayals of a couple as they sever their seven-year marriage and embark on a bitter custody battle.

  • Waiting to Exhale (1995)

    Ahhh revenge. Clearly not a dish best served cold as this tale of four friends navigating love shows; torching your husband’s designer suits inside his fancy car is certainly one way to react when you discover he’s run off with his secretary.

  • Breakfast at Tiffany’s (1961)

    Audrey Hepburn is on the receiving end of a pretty harsh dumping by her fiancé when he tells her, “You call yourself a free spirit, a 'wild thing,' and you're terrified somebody's gonna stick you in a cage. Well baby, you're already in that cage. You built it yourself. And it's not bounded in the west by Tulip, Texas, or in the east by Somali-land. It's wherever you go. Because no matter where you run, you just end up running into yourself." Ouch

  • The Wedding Singer (1998)

    Getting jilted at the aisle is bad enough, but spare a thought for poor Adam Sandler who then has to sing at other happy couple’s weddings where he expresses his grief on stage - until a sugary sweet Drew Barrymore turns up, that is.

  • The First Wives Club (1996)

    Diane Keaton, Bette Middler and Goldie Hawn take Ivana Trump’s advice - ‘don’t get mad, get everything’ - literally when they’re dumped by their husbands for younger women.

  • Bananas (1971)

    If you’e ever tried desperately to convince your beloved not to break-up with you, you’ll understand Woody Allen’s humiliation when he forces his now ex-girlfriend to list all the possible reasons why she doesn't want to be with him. Excruciating stuff.

  • Say Anything (1989)

    Poor John Cusack gives his high-achieving girlfriend his heart in this rom-com directed by Cameron Crowe. And what does she give him? A pen. Doesn’t get much worse than that.

  • White (1994)

    It seems Julie Delpy is quite the heartbreaker as she dumps a Polish immigrant and leaves him franc-less in Paris in this dark comedy of elaborate and morbid revenge.

  • Almost Famous (2000)

    There’s something about the light in Kate Hudson’s hair as she wipes away a tear upon hearing her rockstar lover is done with her - from the mouth of young Rolling Stone writer William Miller - that takes the scene in Cameron Crowe’s coming-of-age film from average to agonizing.

  • Divorce, Italian Style (1961)

    If you thought your last break-up was farcical, observe the extravagant lengths a Sicilian baron goes to to separate from his unattractive but devoted wife in this Italian Oscar-winner. To make matters worse, it’s all so he can run off with his 16-year-old cousin!

  • Swingers (1996)

    A classic 90s relationship comedy that looks at messy break-ups (and obsessive voice-mail messages - how retro!) from the perspective of a (very young and handsome) Ron Livingston and best friend Vince Vaughn that proves you can’t win back an ex unless you’re willing to forget them.

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Stylist Team