25 Best Movies About Heartbreak That You Should Watching Update 08/2022

Movies About Heartbreak

Even the most idealistic of us realize that happy endings don’t always last in real life. There are many stories that begin with a joyful ending and end with a person sobbing alone on the couch while flipping through the channels in search of something to soothe their shattered heart or at least distract them from the pain for a little period.

In other words, sometimes you need a breakup movie rather than a love story. These 25 finest breakup movies (in no particular order) are here to help you process your feelings, exorcise your wrath or inspire you to dust yourself off and go on.

1. Eternal Sunshine of the Spotless Mind

Eternal Sunshine of the Spotless Mind

Try telling someone who’s just come out of a breakup that it’s better to have loved and lost than not have loved at all. Joel (Jim Carrey) tries to erase his ex (Kate Winslet) from his mind, but wonders if some of those memories are worth retaining.

2. Marriage Story

This may be desirable, but it may not always be possible. Charlie (Adam Driver) and Nicole (Scarlett Johansson) endure a brutal custody battle in Marriage Story—and emerge with a new kind of connection centered not on sex and passion but on shared motherhood.

3. High Fidelity

In the aftermath of a breakup, High Fidelity is the film you turn to for solace, and you suspect that at least some of it was your own fault. You may be able to grow up, too, if Rob (John Cusack) does.

4. Forgetting Sarah Marshall

Forgetting Sarah Marshall

If anything, it’s a promise that things will improve. When you’re in a relationship with a well-known TV star, you know it’s going to be hard. Forgetting Sarah Marshall’s Mila Kunis is a great example of a cool girlfriend to love after a breakup.

5. Waiting to Exhale

In Waiting to Exhale, an ex-car boyfriend’s is set ablaze in the name of revenge, but it’s also a soothing reminder that things will get better after all the agony and suffering.

6. Midsommar

There are some breakups where crying isn’t enough, and you need something more dramatic. You may need to travel to Sweden for an obscure death cult’s once-in-a-lifetime festival in order to get your point across in the end of a terrible relationship.

7. Celeste and Jesse Forever

Celeste and Jesse Forever

If two individuals like one other a lot, yet aren’t destined to be in a relationship, it’s tragic. Rashida Jones and Andy Samberg star as a high school sweetheart couple who have been married for seven years, but have decided to separate.

8. Magic Mike XXL

Magic On the other hand, the movie Mike XXL does an excellent job of highlighting one of the positives associated with a breakup: the freedom to join your friends on an epic road trip of sexual pleasure and self-discovery.

9. The Souvenir

Julie (Honor Swinton-Byrne) and Anthony (Tom Burke) had a hopeless relationship depicted in The Souvenir, which shows both the difficulty of separating from a toxic relationship and the scars it leaves behind.

10. Legally Blonde

The character of Elle Woods, played by Reese Witherspoon, is a role model for anyone who has ever been hurt by a cynical ex. Do exactly like she does: In the process of trying to win him back, you’ll find how amazing you are and that you never needed him to begin with. What’s so difficult about this?

11. Casablanca

Casablanca

Only Rick (Humphrey Bogart) and Ilsa (Joan Fontaine) were able to say goodbye to their love in such an epically romantic way (Ingrid Bergman). So why not imagine that we did, if only for a moment. For those times when we’re at our most heartbroken, they have Paris, and we have Casablanca.

12. Gone Girl

Not a breakup, but plenty of commentary on the perils of modern marriage can be found in Gone Girl. Nick (Ben Affleck) and Amy (Rosamund Pike) went from a meet-cute to a fairy tale courtship to…well, you’ll see…and you may decide that you’re better off single.

13. (500) Days of Summer

Tom (Joseph Gordon-Levitt) is a cautionary tale against looking back on past relationships with nostalgia. Until he gets a better look at Summer (Zooey Deschanel), he doesn’t know what went wrong and how to move forward in his life.

14. Crazy, Stupid, Love

More than one character suffers heartbreak in Crazy, Stupid, Love, but the star-studded cast shows you that the perfect one is worth battling for through swoonworthy smooches, grand romantic gestures, and one funny brawl. (You can ignore the antiquated gender roles, if you’d like.))

15. Appropriate Behavior

Appropriate Behavior

Shirin (Desiree Akhavan, who also wrote and directed) and her halfhearted attempts to putting her life back together after she’s abandoned by her relationship (Rebecca Henderson).

16. Swingers

What every newly dumped person needs is a friend who will take them out on the town, gaze at them in their plight, and remind them that they’re so wealthy and they don’t even realize it. Having a friend with the charisma of a young Vince Vaughn is a plus.

17. Closer

If you’ve ever wondered if love exists, or if it’s just a cruel joke designed to ruin people’s lives, this is the movie for you. Clive Owen, Julia Roberts, Jude Law, and Natalie Portman star as four people who can’t stop cheating on each other, which leads to devastating consequences.

18. Blue Valentine

Blue Valentine

In the depths of heartbreak, seeing Blue Valentine is like pressing down on a bruise; it is the suffering that makes it so rewarding. Dean (Ryan Gosling) and Cindy’s (Michelle Williams) gentle beginnings and tearjerking end are juxtaposed in the film.

19. The Wedding Singer

Remembering that breakups aren’t always a bad thing is a comforting thought. When it comes to finding out who your true love is, just ask Robbie and Julia in The Wedding Singer, who were both smitten with each other before realizing that they were engaged to the wrong people.

20. La La Land

Spoilers: Ryan Gosling, king of the breakup film Ryan Gosling plays Sebastian in Crazy, Stupid, Love, whose passionate love affair with Mia (Emma Stone) breaks down over their diverging aspirations, but both of them are transformed for the better by the conclusion.

21. Call Me By Your Name

While the majority of the film focuses on Elio (Timothée Chalamet) and Oliver (Armie Hammer) finding one other, the devastating realization that their relationship can’t endure forever hangs over them all. Reflect on a brief yet passionate relationship by putting this on while you’re listening.

22. The Break-Up

The Break-Up

When Vince Vaughn and Jennifer Aniston, two ex-lovers, fight over sex, it turns into a sad dramedy about repercussions that cannot be undone, even between two people who previously had feelings for each other.

23. Birds of Prey

While going out on your own after a breakup can be difficult, Margot Robbie’s Harley Quinn serves as a reminder that everything is achievable with the right attitude and new pals.

24. The War of the Roses

As Michael Douglas and Kathleen Turner battle it out over the family home in this scathingly comic comedy about divorce, they serve as a cautionary tale against going too far in trying to “win” the split.

25. Scott Pilgrim vs. The World

Scott Pilgrim vs. The World

For better or for worse, your previous relationships are still part of your personal history when you start a new one. For Scott (Michael Cera), that idea is brought to life as he must combat his girlfriend’s seven nasty ex-lovers while also dealing with his own exes.