Heartbreak is something everyone can relate to, even if it isn’t to the stereotypical extent where we’re crying into a bucket of ice cream, or any other number of breakup tropes that have been portrayed a million times in film and television.
Love gained, love lost. It isn’t always the central narrative—more often a supporting storyline to deepen several characters—but there are a handful of seriously good movies where breakups and divorce do play a central role as the driving force or motivation.
As divorce becomes more normalized in Western society, we’ve seen more and more movies about it. But which ones tapped into the pain (and humor) the best? Here are our picks for the best movies about divorce and breakups.
10. The Break-Up (2006)
How could we not include a movie that’s literally titled The Break-Up? In this better-than-expected film, Jennifer Aniston and Vince Vaughn star as a very modern American couple, whose flashy condo in Chicago becomes a battleground of the sexes.
An art dealer and a tour guide, the two couldn’t be more different—hence their relentless bickering. Even when they’re just “roommates,” things are never smooth sailing for the pair. Can they kiss and make up?
Peyton Reed’s breezy romantic comedy is surprisingly funny and full of all the wit you’d expect from a Vince Vaughn movie.
9. Shoot the Moon (1982)
Alan Parker’s family drama Shoot the Moon was inspired by his own encounters with dysfunctional couples. The script was penned in 1971, but took a while to secure funds.
Fortunately, the funds were eventually secured, and Shoot the Moon was released to positive reviews and various awards. It’s a shame it failed at the box office. We still love it though, as Shoot the Moon features searing performances from Albert Finney and Diane Keaton.
This grim domestic comedy follows one unhappy couple, whose bitterness and infidelity traps them in an agonizing cycle—to which their four daughters are witness. Good luck, girls.
8. 500 Days of Summer (2009)
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Hopeless romantic and greeting card writer Tom (played by Joseph Gordon-Levitt) recounts the 500 days leading up to his heart being broken. Summer (played by Zooey Deschanel) is beautiful, eccentric, and fiercely independent—and the two were never meant to be.
A bittersweet comedy-drama from Marc Webb, 500 Days of Summer is a touching and uniquely filmed slice of nostalgic cinema. The dual shots of expectation vs. reality, sketchbook cartoons, and The Smiths soundtrack makes for some artsy viewing yet a real crowd-pleaser.
7. Pieces of a Woman (2020)
You’d be shocked to find out that Vanessa Kirby doesn’t have any kids in real life, at least once you watch her intensely realistic performance of an at-home birth that’ll have you squirming in your seat.
Unfortunately for Martha, the baby doesn’t survive the night. Heartbroken, Martha and Sean (who’s seven years sober up until the tragedy, played by Shia LaBeouf) fail to keep their marriage together.
Martha is reluctantly pushed to file a lawsuit against the midwife, but nothing will bring back her child or her marriage.
Kornél Mundruczó’s gripping drama will leave you speechless, mostly from its knockout performances by Kirby and LaBeouf.
6. Marriage Story (2019)
Charlie Barber is an obsessed artist, whose successful theater company in New York City puts a strain on his once-perfect marriage. When his wife Nicole is offered a starring television role in Los Angeles, the relationship is put under further pressure.
Their young son, Henry, makes their cross-state separation more difficult than it needs to be. But reluctant to get lawyers involved, the couple attempts to reconcile and compromise themselves… They really should have just paid for counseling.
Scarlett Johansson and Adam Driver deliver powerhouse performances as the feuding couple, which director Noah Baumbach punctuates with moments of love and tenderness.
5. Crazy, Stupid, Love (2011)
Ah, that post-divorce glow. When the meek middle-aged Carl Weaver (played by Steve Carell) divorces his cheating wife, his life is reduced to nothing but a sad one-person apartment. At least, until he meets the smooth-talking womanizer Jacob (played by Ryan Gosling) at a bar.
Jacob teaches Carl all the tricks of the trade, and he’s soon making his ex-wife jealous. Directed by Glenn Ficarra and John Requa, Crazy, Stupid, Love is a hilariously clever slice of easy-to-watch comedy, with a twist ending we definitely didn’t see coming.
4. Annie Hall (1977)
Although we aren’t fans of Woody Allen following recent allegations, you can’t escape the brilliance of his early films. Most notably, his classic 1970s romantic comedy film Annie Hall.
Diane Keaton stars in a role specifically written for her, wandering around the streets of Brooklyn with a divorced Jewish comedian. (Three guesses who played that role.)
Annie Hall is a humorous meditation on modern relationships—particularly in the city—that moves at its own pace. Now considered one of the best films ever made, it’s a shining example of Allen’s auteur trademarks.
3. Wildlife (2018)
You’ve probably seen Paul Dano in his gritty roles for 2007’s There Will Be Blood or 2013’s Prisoners. This time, the acclaimed actor steps behind the camera for his stunning directorial debut with Wildlife.
Starring Hollywood heartthrob Jake Gyllenhaal, Wildlife follows a struggling couple in a suburban town in 1960s Montana.
Jeanette (played by Carey Mulligan) confides in their teenage son about his parents’ crumbling marriage, while Jerry (played by Jake Gyllenhaal) takes a low-paying job fighting fires. A rhythmic portrait of a family in crisis, Wildlife is cleanly and carefully directed.
2. Eternal Sunshine of the Spotless Mind (2004)
It’s one thing to take a breakup badly. It’s another thing to literally erase your ex-partner from your memory.
Michel Gondry’s sci-fi drama Eternal Sunshine of the Spotless Mind takes us on a journey through the mind, in which Joel Barish (played by Jim Carrey) undergoes surgery to remove all traces of Clementine (played by Kate Winslet) from his brain.
But he starts to regret it halfway through and tries to run from the impending black holes of his memory.
Jim Carrey, Kate Winslet, Kirsten Dunst, Mark Ruffalo, Elijah Wood, and Tom Wilkinson make up the all-star cast, fusing elements of psychological drama with trippy surrealism in a non-linear narrative.
1. Kramer vs. Kramer (1979)
Before Meryl Streep was the highly respected Hollywood star of today, she played a supporting role in Robert Benton’s legal drama Kramer vs. Kramer. When Joanna Kramer suddenly ups and leaves, her workaholic husband is left to care for their young son.
Unaccustomed to the domestic life of fatherhood, Ted (played by Dustin Hoffman) initially struggles under the weight of his new responsibilities. However, their father-son bond ends up stronger than ever… until Joanna reappears on the scene with a lawyer.
Based on Avery Corman’s novel, Kramer vs. Kramer came at a poignant time in history for feminism, custody rights, and single parenting.