20 Essential Break Up Movies

by eHarmony Staff

20 Essential Break Up Movies

1. Eternal Sunshine of the Spotless Mind

This offbeat romantic comedy (which won an Oscar for Best Original Screenplay) stars Jim Carrey as Joel, who opts for a procedure in which memories of his girlfriend, Clementine (Kate Winslet), are erased after he learns she’s already had the surgery done. But as his doctor begins to wipe out traces of Clementine, Joel decides he doesn’t want to lose what’s left of their relationship, so he squirrels away the memories somewhere else in his brain.

2. Kramer vs. Kramer

Ted (Dustin Hoffman) is a career-driven yuppie — until he finds out his wife (Meryl Streep) is leaving him and their 6-year-old son. Ted soon finds that he loves being a full-time parent, but then his wife reappears to reclaim the boy. Poignant and beautifully acted, the movie swept the 1979 Academy Awards, winning Oscars for Hoffman and Streep, plus Best Picture, Best Director and Best Screenplay honors.

3. Annie Hall

Listen closely and you can actually hear the stress hormones pumping through the bodies of the characters in Annie Hall. Woody Allen’s real, funny ode to love among twitchy city dwellers scooped up Oscars for Best Picture, Best Direction, Best Actress (Diane Keaton) and Best Screenplay. And don’t miss cameos of not-yet-stars Jeff Goldblum, Shelley Duvall and Sigourney Weaver.

4. Chungking Express

Hong Kong director Kar Wai Wong established a unique style with this cerebral film that tells two somewhat similar but unrelated stories about loneliness and disconnection in the big city. In the first story, a policeman pines after his former girlfriend and gives himself 30 days to find another woman; in the second story, another policeman catches the eye of an attractive waitress, who’s intent on completely rearranging his life.

5. High Fidelity

Vintage record store owner Rob Gordon (John Cusack) has been dumped by his girlfriend, Laura (Iben Hjejle), because he hasn’t changed since they met. In an attempt to figure out where things went wrong, Rob revisits his top five breakups of all time. As he seeks out his former lovers to find out why they dumped him, he continues his efforts to win Laura back. Based on the Nick Hornby novel, the film is a clever, funny tribute to the music scene.

 

6. The War of the Roses

This battle of the married sexes played out under director Danny DeVito’s jaundiced eye is what The Washington Post termed, “A yuppie Armageddon, an explosion of empty values and curdled peevishness.” Oliver Rose (Michael Douglas) is losing control over his wife, Barbara (Kathleen Turner), after 17 years of marriage. The irreconcilable difference is their house. Neither wants to move out, so that means all-out war!

7. White

Julie Delpy stars in Krzysztof Kieslowski’s dark comedy (the middle segment in his “three colors” trilogy) about the price of passion. Polish immigrant Karol Karol (Zbigniew Zamachowski) is humiliated in a public courtroom by his wife (Delpy) during their divorce proceedings. Shamed and brokenhearted, he finds an ally in a fellow countryman. The two concoct a way back to post-Communist Poland, where Karol sets about rebuilding his life.

8. Broken Flowers

After being dumped by yet another girlfriend (Julie Delpy), Don Johnston (Bill Murray) vows he’ll be alone forever. But when a mysterious unsigned letter arrives in the mail, he’s surprised to learn he has a 19-year-old son. With no idea who the mother could be, Don sets out on a cross-country journey to confront his past, surprising a series of old flames (Frances Conroy, Jessica Lange, Sharon Stone and Tilda Swinton) along the way.

9. Swingers

In director Doug Liman’s career-making look at twenty-something guys, struggling comedian Mike (Jon Favreau) despairs over his love life, so his four pals, fellow Hollywood hopefuls, pump up his nightlife. Buddy (Vince Vaughn), offering dubious lessons on “babes,” even whisks Mike to Vegas. Although their attempts at living la vida loca seldom work out as fantasized, Mike meets one woman (Heather Graham) who might finally break his funk.

10. The Squid and the Whale

Jeff Daniels makes for a haunting Brooklyn professor who’s well past his prime, and Laura Linney is his writer wife on the brink of stardom in Noah Baumbach’s honest look at the disintegration of a marriage. With their lives headed for distinctly opposite directions, the two can’t help but be acrimonious about their impending separation. Unfortunately, their two children are stuck in the middle of the emotional warfare.

 

11. Forgetting Sarah Marshall

After his TV star girlfriend, Sarah Marshall (Kristen Bell), breaks his heart, Peter (Jason Segel) wants nothing more than to enjoy his vacation in Hawaii. One problem: Sarah’s vacationing at the same resort he is, and even worse, she’s bringing her new beau. Produced by Judd Apatow (Knocked Up, Superbad), this hilarious comedy also stars Mila Kunis, Paul Rudd and Bill Hader.

12. Better Off Dead

After his girlfriend (Amanda Wyss) ditches him for a boorish ski jock, Lane (John Cusack) decides that suicide is the only answer. However, his increasingly inept attempts only bring him more agony and embarrassment. Filled with the wildest teen nightmares, a family you can’t help but identify with and a host of wonderful comic characters, Better Off Dead is a masterful look at those painfully funny teen years.

13. An Unmarried Woman

A groundbreaking film at the time of its release, director Paul Mazursky’s poignant portrayal of a woman dealing with the dissolution of her marriage won many honors, including Oscar nominations for Best Picture, Screenplay and Actress (Jill Clayburgh). When her seemingly perfect husband (Michael Murphy) leaves her for another woman, devastated wife Erica (Clayburgh) must find untapped strength within herself to build a new life.

14. Dodsworth

To escape an empty nest, an automobile tycoon (Walter Huston) and his forty-something wife (Ruth Chatterton) plan a luxurious vacation in Europe. But as Mrs. Dodsworth embarks on a series of indiscretions — including a romance with a gigolo — it becomes apparent that the couple’s plans for their golden years don’t mesh. From director William Wyler, the film is based on the best-selling novel by Sinclair Lewis and an acclaimed stage play.

15. Diary of a Mad Black Woman

Helen McCarter (Kimberly Elise) is happy and completely satisfied with her life: She has a doting husband, Charles (Steve Harris), an impressive home in their native Atlanta complete with a swimming pool and tennis courts, and anything else money can buy. But the night before her 18th anniversary, Charles kicks her out of their home and replaces her with his mistress, calling into question what Helen had long considered a solid marriage.

 

16. Breaking Up

Based on a two-person play by Michael Christofer (who also wrote the screenplay), Breaking Up is a series of charming vignettes that reveals the on-again, off-again relationship between modern lovers Steve (Russell Crowe) and Monica (Salma Hayek). Their emotional bond is so intense that it borders on the manic-depressive, and they constantly fluctuate between romantic euphoria and ennui … like many of the rest of us!

17. Divorce American Style

Television sitcom director Norman Lear helms this dark comedy about the paralyzing process of divorce. Ex-couple Dick Van Dyke and Debbie Reynolds come to realize that after the trials and tribulations of dating, debilitating alimony payouts and commiserations with fellow divorcees, married life wasn’t so bad after all. Co-stars Eileen Brennan, Joe Flynn, Van Johnson, Jean Simmons and Jason Robards.

18. My Super Ex-Girlfriend

It’s a bird! It’s a plane! It’s a bitter superwoman scorned! Fed up with his manipulative girlfriend, Jenny Johnson (Uma Thurman), New Yorker Matt Saunders (Luke Wilson) gives her the heave-ho and moves on with his life, leaving the heartbroken Jenny — aka G-girl — to do everything within her superpowers to humiliate Matt. Director Ivan Reitman’s slapstick fantasy comedy also stars Anna Faris, Rainn Wilson and Eddie Izzard.

19. The Belly of an Architect

Jealousy rears its ugly head in this searing drama about a workaholic architect, Stourley Kracklite (Brian Dennehy), who’s traveling to Rome for a job. On this trip, however, he’s brought his wife (Chloe Webb), who’s grown distant and whom he begins to suspect is in love with another man. But that’s not all: Kracklite also thinks his wife is plotting to kill him so she can live happily ever after, but he won’t let her get away with it.

20. The Break-Up

Once blissfully in love, Gary (Vince Vaughn) and Brooke (Jennifer Aniston) find themselves up in arms over custody of their upscale Chicago condo when petty spats about lemons and dirty dishes end their romance. An escalating battle of the exes ensues as Gary and Brooke continue to live under the same roof … while cooking up schemes to drive each other off the premises. Judy Davis delivers a wickedly funny performance as Brooke’s diva boss.

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