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 in the plot.
As divorce grows increasingly normalized in Western society, we've seen more movies made about it. Here are my picks for the best movies about divorce and breakups worth watching.
15. The Break-Up (2006)
Directed by Peyton Reed
Starring Jennifer Aniston, Vince Vaughn, Jon Favreau
Comedy, Drama, Romance (1h 46m)
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 flick.
14. Shoot the Moon (1982)
Directed by Alan Parker
Starring Albert Finney, Diane Keaton, Karen Allen
Drama (2h 4m)
Alan Parker's family drama Shoot the Moon was inspired by his own encounters with dysfunctional couples. The script was penned in 1971, but it took a while to secure funds.
Fortunately, funding was 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 trap them in an agonizing cycle—to which their four daughters are witness. Good luck, girls.
13. Closer (2004)
Directed by Mike Nichols
Starring Julia Roberts, Natalie Portman, Jude Law, Clive Owen
Drama, Romance (1h 44m)
Closer isn't about a love triangle so much as a love square. Based on a play, which itself was based on an opera, Closer features a dazzling cast of Jude Law, Natalie Portman, Julia Roberts, and Clive Owen, all competing for each others' affections.
You'd think a man writing an entire book about you would mean you're safe from betrayal. Wrong! While marketing his new book, Dan proposes an affair to another woman... one who's already in a relationship.
The subsequent cheating, brooding, and sneaking around results in divorce on one side and a breakup on the other. It's all very complicated, but navigated smoothly via clean direction from Mike Nichols.
12. 500 Days of Summer (2009)
Directed by Marc Webb
Starring Zooey Deschanel, Joseph Gordon-Levitt, Geoffrey Arend
Comedy, Drama, Romance (1h 35m)
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 make for some artsy viewing, yet it's a real crowd-pleaser.
11. Pieces of a Woman (2020)
Directed by Kornél Mundruczó
Starring Vanessa Kirby, Shia LaBeouf, Ellen Burstyn
Drama (2h 6m)
You'd be shocked to learn that Vanessa Kirby doesn't have any kids in real life after you watch her intensely realistic performance of an at-home birth that'll have you squirming in your seat.
Unfortunately, the baby doesn't survive the night. The heartbroken Martha and Sean (who's seven years sober up until the tragedy, played by Shia LaBeouf) fail to keep their marriage together in the aftermath.
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 for the knockout performances by Kirby and LaBeouf.
10. Marriage Story (2019)
Directed by Noah Baumbach
Starring Adam Driver, Scarlett Johansson, Azhy Robertson
Drama, Romance (2h 17m)
Charlie Barber (played by Adam Driver) is an obsessed artist whose successful theater company in New York City puts a strain on his once-perfect marriage.
When his wife Nicole (played by Scarlett Johansson) is offered a starring television role in Los Angeles, their relationship is stressed further. And their young son Henry (played by Azhy Robertson) makes their cross-state separation more difficult than it needs to be.
Reluctant to get lawyers involved, the couple attempts to reconcile... 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.
9. Crazy, Stupid, Love (2011)
Directed by Glenn Ficarra and John Requa
Starring Steve Carell, Ryan Gosling, Julianne Moore
Comedy, Drama, Romance (1h 58m)
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.
8. Blue Valentine (2010)
Directed by Derek Cianfrance
Starring Ryan Gosling, Michelle Williams, John Doman
Drama, Romance (1h 52m)
Michelle Williams and Ryan Gosling spent an entire month living together in preparation for their roles as young Brooklyn lovers in Blue Valentine—and it paid off.
To be fair, they start the movie as young. Then, director Derek Cianfrance switches between time periods, from when they first got together to their shambles of a marriage years later.
The high school dropout and doctor-in-training end up drinking and screaming their way through life on a tight budget. By the end, they're signing divorce papers... despite arguably still being in love.
7. La La Land (2016)
Directed by Damien Chazelle
Starring Ryan Gosling, Emma Stone, Rosemarie DeWitt
Comedy, Drama, Music (2h 8m)
Three Ryan Gosling movies in a row? He's on fire! Though maybe not in a good way if all he's doing is getting dumped...
La La Land has one of the best movie endings of the past decade, tricking us into thinking Mia (played by Emma Stone) and Sebastian (played by Ryan Gosling) will live happily ever after, only to pull the rug out from beneath us. It's like Atonement, but without the war-torn tragedy.
La La Land is a musical that even musical-haters can enjoy, where we tap dance across the Hollywood Hills to the romance of the stars. But with both our protagonists having such big dreams, ultimately they must choose between love and their careers.
6. Annie Hall (1977)
Directed by Woody Allen
Starring Woody Allen, Diane Keaton, Tony Roberts
Comedy, Romance (1h 33m)
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 Annie Hall.
Diane Keaton stars in a role specifically written for her, where she wanders 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 ones that take place in big cities—that moves at its own pace. Now considered one of the best films ever made, it's a shining example of Woody Allen's auteur trademarks.
5. Manchester By the Sea (2016)
Directed by Kenneth Lonergan
Starring Casey Affleck, Michelle Williams, Kyle Chandler
Drama (2h 17m)
Losing a child has to be the biggest challenge any romantic couple can face, and it's so bad that most marriages don't survive such a tragedy—no matter how much they love each other.
Written and directed by Kenneth Lonergan, Manchester By the Sea is one of the most gut-wrenching depictions of parental grief in cinema.
Casey Affleck stars as the now (understandably) depressed father Lee, who accidentally left his house one day without a fireplace guard in place. You can probably guess what happened after that...
Lee's ex-wife Randi (played by Michelle Williams) doesn't exactly blame him for the tragedy, but she also can't stand to be near him. No one can blame Lee for leaving his hometown and getting away from it all.
But when he's called to become the guardian of his orphaned nephew, Lee must return home and face his ex, his past, and his demons.
4. Wildlife (2018)
Directed by Paul Dano
Starring Ed Oxenbould, Jake Gyllenhaal, Carey Mulligan
Drama (1h 45m)
You've probably seen Paul Dano in his gritty roles for 2007's There Will Be Blood or 2013's Prisoners. But in Wildlife, the acclaimed actor stepped behind the camera for a stunning directorial debut.
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 their 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 to great success.
3. Eternal Sunshine of the Spotless Mind (2004)
Directed by Michel Gondry
Starring Jim Carrey, Kate Winslet, Tom Wilkinson
Drama, Romance, Sci-Fi (1h 48m)
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 comprise the all-star cast in this non-linear story that fuses elements of psychological drama with trippy surrealism.
2. Call Me By Your Name (2017)
Directed by Luca Guadagnino
Starring Timothée Chalamet, Armie Hammer, Michael Stuhlbarg
Drama, Romance (2h 12m)
Call Me By Your Name is a little different from the movies on this list. There's no "official" breakup because Elio (played by Timothée Chalamet) and Oliver (played by Armie Hammer) were never properly together.
Instead, the two shared a secret bond that was practically forbidden for several reasons: they were years apart in age, Elio was still in the closet, and Oliver was basically an employee of Elio's father...
In adapting André Aciman's coming-of-age novel, Luca Guadagnino transports us to the glorious Italian countryside where the academic Perlman family goes to vacation every year.
Call Me By Your Name perfectly encapsulates the feeling of summer love and the feeling of your first heartbreak. The final shot of Elio crying in front of the fireplace has become legendary, proving again that less is often more when it comes to cinematic impact.
1. Kramer vs. Kramer (1979)
Directed by Robert Benton
Starring Dustin Hoffman, Meryl Streep, Jane Alexander
Drama (1h 45m)
Before Meryl Streep was the highly respected Hollywood star she is 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 before him 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.
