Top 10 Breakup Movies

In this dark comedy, divorce lawyer Gavin D’Amato, played by Danny DeVito, tells his client the tale of his friends, the Roses, and how their idyllic marriage fell apart. As their divorce moves forward, both of the Roses become more and more obsessed with one-upmanship and hurting each other as much as possible. Gavin makes it clear that when problems arise, the selfish route is the wrong path, and that it’s better to at least attempt to make amends rather than trying to “win” the breakup and keep score. The result was a critical and commercial success that also earned the leads Golden Globe nominations.

When Jacob and Anna meet, their attraction is almost instantaneous, and they quickly fall in love. Unfortunately for the couple, Anna is only in America on a student visa, and will have to return to England soon enough. Over the next few years, these star-crossed lovers come together and break up a number of times, not only because of geography, but because of their own issues. For better or worse, they seem to be the love of each other’s lives and can never seem to stay apart (or together) for long and their story, partly based on the director’s experiences, made for this well-received romantic drama that earned its young leads a number of awards.

This iconic ‘80s film shows the courtship of two opposites; a rich socially awkward valedictorian, Diane, and an easygoing underachiever, Lloyd. Although things seem to go well for the couple at first, social standings, as well as pressure from her father, cause the couple to break up. In an attempt to win her back, Lloyd pulls a stunt that has since gone down in movie history, while the romantic comedy-drama itself has been hailed as one of the sweetest, most thoughtful and funniest movies of 1989.

After getting dumped by his longtime girlfriend, the famous actress Sarah Marshall, Peter Bretter is having a bit of a hard time; he just can’t seem to get Sarah off his mind. He decides that the best thing for him is a vacation to Hawaii; unfortunately for Peter, Sarah just happens to be staying at the same resort with her new rock star boyfriend. Jason Segel, who both wrote and starred in the rom-com, gives us a hilarious, but surprisingly touching, film about moving on and believing in yourself. Critics and moviegoers agreed, with “Forgetting Sarah Marshall” making over $105 million at the box office.

This aptly named rom-com takes a lighthearted and humorous approach to issues including, but not limited to, heartbreak, infidelity, and unrequited love. The soon-to-be-divorced Cal strikes up an unusual friendship with a young player, Jacob, who shows the middle-aged man a few tricks to pick up women. Things get complicated when Jacob meets a girl who makes him rethink his philosophy on women, and even more complicated when it turns out that certain people in this story share unexpected connections. Ultimately, the film shows the ups and downs of falling in and out of love, and earned critics’ favors, box office millions and a Golden Globe nod for Ryan Gosling.

Rob, a record storeowner played by John Cusack, is going through yet another in a long line of breakups, and is experiencing a bit of a quarter life crisis. He decides to look back at his prior relationships, romanticizing some, all while pining over his most recent ex Laura. Eventually, Rob even makes a top 5 list of most significant breakups (something we can appreciate here at WatchMojo!) and contacts a few of his exes, trying to figure out why he can’t seem to keep a good thing going. With its strong performances and great soundtrack, “High Fidelity” also received mostly positive reviews from critics.

Everyone has had a relationship that they would like to forget. In this romantic sci-fi comedy drama, a fictional procedure allows you to do just that. So after Joel’s ex Clementine erases him entirely from her memory, he impulsively decides to do the same to her. The film implies that it is never better to forget someone once loved; we should instead remember both the good times as well as the bad, and when we choose to forget someone we are losing a piece of our own history and ourselves. Making over 3 times its budget at the box office, “Eternal Sunshine” also scored high with critics and an Oscar for Best Screenplay.

Derek Cianfrance’s beautiful and heartbreaking masterpiece shows a young couple, with the narrative alternating between their hopeful courtship and the last days of their marriage several years later. Unlike many of the other films on this list, both characters are given equal importance, and presented as good, yet flawed people. Their breakup is not caused by a defining moment or character flaw; rather it’s a slow and sad decline to the realization that they are no longer what they once were. Its tough, but realistic portrayal of love gone wrong earned its actors multiple award nominations. Just make sure you’ve got a box of tissues for this one.

Right from the start, it’s made clear that this is not a love story. By following a hopeless romantic, Tom, and the ups and downs of his idealized relationship with the aloof beauty, Summer, this romantic comedy-drama shows the difference between a person’s perceptions of his life versus reality. We see various points in the 500 days of Tom’s infatuation, presented out of order, ranging from Tom being completely in love with Summer one moment and miserable and furious with her in the next. This rarely used storytelling structure helped “500 Days of Summer” become a sleeper hit, while its portrayal of a guy’s perspective on heartbreak was a fresh spin on the rom-com genre.

Before we unveil our top pick here are a few honorable mentions:
- “In the Mood for Love” (2000)
- “When Harry Met Sally…” (1989)
- “The Way We Were” (1973)
- “French Kiss” (1995)

Without “Annie Hall,” chances are that a lot of the films on this list wouldn’t even exist. The romantic comedy, which stars Woody Allen and Diane Keaton, is a pioneer of non-sequential storytelling. Like many of the movies that emulate it, “Annie Hall” examines various moments in the couple’s relationship and its deterioration, jumping to different points non-chronologically. Its realistic portrayal of the shifts in a relationship and its eventual end earned “Annie Hall” an Oscar for Best Picture, among 3 other Academy Awards, and is often considered one of Allen’s best works.

Do you agree with our list? Or did we break your heart by leaving something off? What are your favorite breakup movies? For more heart-wrenching Top 10s published daily, be sure to subscribe to WatchMojo.com.