Annie Hall (1977)
Arguably Woody Allen’s best film, Annie Hall documents the entirety of a relationship (partly inspired by real-life ex-lovers Allen and Diane Keaton), with enough lighthearted and sarcastic humor to balance out the misery.
Breaking Upwards (2009)
Real-life couple Daryl Wein and Zoe Lister-Jones co-wrote and co-starred in this indie comedy about a pair of Brooklynites (named Daryl and Zoe, by the way) who try to strategize about their impending breakup by settling into an open relationship.
Broadcast News (1987)
James L. Brooks’ follow-up to Terms of Endearment follows a trio of Washingtonians working at a local news station who struggle with their own ambitions as well as their romantic frustrations. It teaches a good lesson: It’s not you, it’s everybody.
Eternal Sunshine of the Spotless Mind (2004)
Perhaps the ultimate in breakup movies, this mind-melding drama shows the complications of getting what everyone wants after going through a breakup — being able to forget everything about the former partner — and features some of the best best acting from its terrific ensemble cast (but especially Kate Winslet).
(500) Days of Summer (2009)
This Annie Hall for millennials is both beloved and reviled (I’m in the latter camp, honestly), but its twee sensibilities might be charming enough to make you forget about your own discomfort for at least an hour or two.
Forgetting Sarah Marshall (2008)
Jason Segel wrote and starred in this tale of a man who tries hard to forget his famous ex-girlfriend, only to discover that she and her rock-star boyfriend are staying next door at a Hawaiian resort. Hilarity and awkward moments of nudity ensue.
Great Expectations (1998)
Sure, director Alfonso Cuaron took some liberties with Charles Dickens’ classic novel, but one of the underrated film’s many brilliant elements includes the wonderful Anne Bancroft as a menacing, salsa-dancing Miss Havisham, proving that eternal unhappiness can also be kinda groovy.
Nora Ephron’s second husband, Carl Bernstein, cheated on her when she was pregnant with their second child. Naturally, she wrote a novel about it and then Mike Nichols made a movie about it. Having Meryl Streep play you at your most vulnerable might be everyone’s dream.
High Fidelity (2000)
Nick Hornby’s novel about a sad-sack record store owner gets an Americanized film treatment. John Cusack plays Rob Gordon with sad-puppy-eyed perfection as the character looks back at his former relationships in the wake of yet another breakup.
Kramer vs. Kramer (1979)
Meryl Streep proved early in her career that she was a force to be reckoned with, and she picked up her first Oscar for her portrayal of a woman trying to gain custody of her son after leaving him and her husband (played by Dustin Hoffman, who also won an Oscar).
Rid of Me (2011)
This bizarre, awkward, and unsettling film is perhaps one of the most uncomfortable depictions of a broken marriage and the toll a breakup can take on one’s already-unstable emotions.
Meryl Streep again plays a villain in this trashy cult favorite starring Roseanne Barr as a housewife who exacts revenge on her husband after he leaves her for a more beautiful and more successful woman.
Sliding Doors (1998)
Sometimes finding your boyfriend in bed with another woman can do wonders for your haircare! It all depends, really, on the serendipitous reliability of the London Underground.
The Squid and the Whale (2005)
Noah Baumbach’s autobiographical story of two teenage boys in 1980s Park Slope dealing with their literary parents’ divorce offers some stellar performances from Laura Linney and Jeff Daniels, and it also accurately portrays the bitterness felt by anyone close to a major breakup.
An Unmarried Woman (1978)
Paul Mazursky’s comic drama follows an Upper East Side woman (played by the remarkable Jill Clayburgh) who goes through a period of healthy (and, to be honest, pretty sexy) self-actualization after her husband leaves her for a younger woman.
The Upside of Anger (2005)
This is a pretty dumb movie, to be honest, but I’ll always have a soft spot for what is one of Joan Allen’s greatest roles. After her husband disappears, a woman must confront her rage as she comes to recognize the end of her marriage.
The War of the Roses (1989)
Look, if you make it out of your breakup without falling to your death from your chandelier, rest assured that you’re doing something right.
The Way We Were (1973)
Sydney Pollack’s romantic weeper starring Robert Redford and Barbra Streisand proves that not all great loves are meant to last, but memories, on the other hand, will always stick around.
Julie Delpy stars in the second film in Krzysztof Kieślowski’s Three Colors trilogy as a young French woman who divorces her Polish immigrant husband, which then leads him to obsessively attempt to win her back so he can fake his own death and have her framed for murder. (The good news: it’s a comedy!)
Wuthering Heights (1939)
Sometimes when you’re in the midst of a breakup you just need to watch a movie where everyone ends up not just miserable but also dead. Cathy and Heathcliff go through it all so you don’t have to.