Lemondrop

The 10 Worst On-Screen Break-Ups

Cruel Intentions – "I thought I was in love with you but it was just a lie. I feel nothing. I just... I just wanted to see what you were like in bed. I don't know how to make this any clearer to you. You mean nothing to me! You were just a conquest." Those are not the final words you care to hear from someone you love, but that's what Ryan Phillippe said to Reese Witherspoon when he broke up with her to spare her from his reckless life. I just hope he was nicer in their real-life break-up.


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Dreamgirls - How would you feel if someone dumped you via song and dance? Curtis (Jamie Foxx) not only breaks up with Effie (Jennifer Hudson) by breaking out into chorus, but proceeds to replace her with Deena (Beyonce Knowles) as the lead singer in his group, as well as his girlfriend. Curtis sings to her, "But you're getting out now. I'm not building this group to have you tear it apart. Go ahead and rant and scream and shout. Don't worry baby, I'll buy you out." Deena replies, musically, "And now your telling me it's all over?" The group all sing back in perfect harmony, "And now we're telling you it's all over." Cue the chorus of heartbreak.

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Chasing Amy -- Affable Holden (Ben Affleck) falls for lesbian rock chick Alyssa (Amy Lauren Adams). Initially, they're just friends, but after one of the most endearing "turns out, I love you" speeches ever put on film, they start dating. Things are rocky as Holden tries to deal with his girlfriends past and sexuality, until he decides the only solution is to ... have a threesome with his roommate? It sounds silly, but its hard not to root for this mismatched pair, even after his ridiculous suggestion that is beyond painful to watch.


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Gone With the Wind - Scarlett (Vivien Leigh) and Rhett (Clark Gable). Has there ever been a bigger on screen break up? Lord knows why that wonderful man loved such a silly little princess, but he did. Which is why its soul crushing to watch as she spends most of the film googly eyed over Ashley (Lesley Howard), some man she A) would never have a chance with and B) doesn't really love anyways. She eventually realizes this, runs home to tell Rhett, who is already on his way out of her life. But despite her begging and asking what she'll do without him, all she gets is one of the most famous movie lines of all time: "Frankly my dear, I don't give a damn."

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10 Things I Hate About You - Patrick (Heath Ledger) and Kat (Julia Stiles) were made to be together, if only in movie heaven. But like many film couples, in order to make it they have to go through one helluva breakup -- which includes a nasty fight at the prom, a football stadium serenade, a public poetry reading and Patrick coughing up a lot of cash to buy his girl a guitar. Sure, its a lot of work, but thats what you get when you're originally getting paid to date a girl before you eventually fall for her. Confused? Take our word for the "made for each other" thing, and check it out.

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Good Will Hunting - Deathly afraid of emotional attachments and his own heart, Will (Matt Damon) looks his girlfriend Skylar (Minnie Driver) straight in the face and tells her he doesn't love her. We know he doesn't mean it, but after everything she put up with from him, it's hard to believe he does it. She moves to California, he eventually grows up, and the film closes with him driving out to find her. Good boy.

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The Break-up – this movie is the modern version of War of the Roses, except it's more a war of real-estate. Upon breaking up Jennifer Aniston and Vince Vaughn both refuse to move out of their shared Chicago condo, taking them from bickering lovers to all out battling roommates. We feel their pain; good real estate in a bustling city is hard to find.

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French Kiss – Meg Ryan's fiancé, Timothy Hutton goes to France for a convention, but her extreme fear of flying prevents her from joining him. After a mere three days in the most romantic city in the world, Hutton calls and tells her, "I met this woman, this apparition, this goddesse," and proceeds to terminate their engagement... over the phone. Nice one, asswipe.

The Way We Were - Katie (Barbara Streisand) and Hubbell (Robert Redford) were as unlikely a couple as any. Her being an anti-war Jew, him an apathetic WASP, and all. The film shows their turbulent relationship through flashbacks, including their heartbreaking but inevitable breakup. While it goes down in flames seemingly because Hubbell cheats on Kate with an ex while she's pregnant, the truth (and heartbreak) comes in knowing that Hubbell simply could never live up to the person Kate expected of him, and he was exhausted from trying. Though, we can't imagine trying to live with Streisand everyday either.

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Waiting to Exhale – Telling your wife that you're leaving her for your secretary as she's getting ready for your company banquet is not just bad timing, it's hella rude. Michael Beach tells Angela Bassett that he's leaving her after eleven years of marriage. She responds with pyromania and selling what didn't burn. He later tries to buy her off, "I am prepared to offer you $300,000 cash, today." "Your children aren't for sale," she responds. Not to mention you can't buy off a broken heart.


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