Breaking up is hard to do but when added to a film, it can create something special and become one of the 10 best break up movies of all time. Whether the movie is a straight breakup film, a black comedy or a fantastical experimental film, all the movies on this list remain interesting efforts.
- “Eternal Sunshine of the Spotless Mind.” Michel Gondry directs this Charlie Kaufman penned movie, one of the best break up movies of all time. Jim Carrey and Kate Winslet star as a couple who falls in and out of love in a world where a company sells the ability to erase anyone out of their mind. It is a groundbreaking and devastating look at lost love.
- “High Fidelity.” John Cusack stars in this movie, one of the best break up movies, which shows how many ways a man can lose a woman. Cusack counts down the Top 5 of almost everything in his life including the girls who broke up with him.
- “(500) Days of Summer.” Marc Webb directs this nonlinear movie, one of the best break up movies of all time. Joseph Gordon Levitt plays a boy who meets the girl of his dreams and then the movie shows their ups and downs, all mixed up and out of order, until the big break up finally occurs.
- “War of the Roses.” Danny DeVito directs this addition to the best break up movies of all time. Michael Douglas and Kathleen Turner star as a couple who chooses to divorce and then set out to make each other’s life a living hell. The movie is the ultimate break up movie as the two set out to prove their marriage was ‘til death do they part.
- “Annie Hall.” Woody Allen’s greatest movie is also one of the best break up movies of all time. Alvy Singer is a neurotic comedian who talks to the audience about the women he fell in love with and then lost. The movie won the Best Picture Oscar in 1978.
- “Sliding Doors.” “Sliding Doors” shows there are two sides to every story. In parallel worlds, the lead character catches her husband cheating on her and then doesn’t catch her husband cheating on her. The movie then follows each result to the end, making it one of the most unique best break up movies of all time.
- “Say Anything.” Cameron Crowe’s directorial debut is about a young man who sets out to try to win over a girl. She agrees to date him but when her father shows disapproval, breaks up with him. The movie is one of the best break up movies but, unlike most, ends with a happy ending as he finally wins her over.
- “Swingers.” Jon Favreau and Vince Vaughn became major movie stars because of this movie. Favreau’s character is dumped by his girlfriend and Vaughn’s devil-may-care character tries to show his friend there are plenty of fish in the sea. This is one of the best break up movies as Favreau spends most of the movie lost without his former girlfriend.
- “The Break Up.” The name says it all as this is one of the best break up movies, if for nothing else than its title alone. The movie follows a character through the breakup and is one of the more in-depth looks at what all a break up entails. The movie stars Vince Vaughn and Jennifer Aniston.
- “My Super Ex Girlfriend.” Luke Wilson and Uma Thurman star in this comic book spoof movie about a normal guy who dates a woman with super powers. When he decides to break off the relationship, she becomes quite psychotic, making this one of the funnier best break up movies on the list.
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