The 15 Best Break-Up Movies Of All Time

As humans, there are a lot of ways we try to cope after someone ends a relationship with us. Some of us eat entire pints of ice cream, while others spend their time at the gym or trying on new clothes. Some of us simply listen to Taylor Swift's entire discography on repeat. However, few things can take you out of those repetitive patterns of heartbreak like a good, relatable film about love lost or taken away. 

From serious, Oscar-bait dramas to laugh-out-loud-funny rom-coms, plenty of films perfectly capture the universal experience of going through a break-up, whether you're an adult struggling with a family-splitting divorce or a teenager experiencing your first crushing heartbreak. These 15 films might have happy endings, bittersweet endings, or just plain sad endings, but they might in some way offer comfort for those who are currently going through the summer without another person by their side. 

"When Harry Met Sally..." might be considered by many to be one of the greatest romantic comedies of all time, but it's easy to forget until you re-watch it that the movie is actually primarily about its titular characters dealing with break-ups. After reconnecting as adults, the sarcastic Harry (Billy Crystal) and uptight Sally (Meg Ryan) become best friends, bonding over their shared heartbreaks and navigating newly single lives as adults in New York City. While Harry wallows in his misery and sleeps with anyone he can to forget about his ex-wife, Sally's mature and unbothered approach represses her true feelings.

Ultimately, the film leads toward an ending where, after a misguided hook-up results in Harry and Sally falling out, Harry races through New York on New Year's Eve to profess his love to her at midnight. It's a deeply romantic ending, but the film doesn't ignore how world-shattering and repercussive the effects of a break-up can have on a person, but not even that grief can stop true love between two seemingly opposite friends. 

Later this summer, "The War of the Roses" is getting a modern reinterpretation, titled "The Roses," starring Olivia Colman and Benedict Cumberbatch. Until we see if this remake is better than the original, we can highly recommend this 1989 film. "The War of the Roses" stars Kathleen Turner and Michael Douglas as Barbara and Oliver Rose, a wealthy couple whose picture-perfect marriage suddenly devolves into a nasty and vicious divorce. While Douglas and Turner do amazing work, it's also one of the best Danny DeVito movies, as the "It's Always Sunny in Philadelphia" star plays Oliver's lawyer and the film's narrator (alongside duties as the film's director). 

Obviously, this film is a lot more comedic and absurd than most of the other break-up movies on this list, but it might be the perfect, cathartic palate cleanser for the recently broken-up with. At the very least, it might send you down the rabbit hole of binge-watching all the other great films that DeVito has directed, including "Throw Momma from the Train" and "Matilda." 

If you're not a student of film history, odds are you probably haven't seen "Chungking Express." If that's the case, prepare yourself for one of the best international films of all time. Directed by Hong Kong filmmaker Wong Kar-wai, "Chungking Express" was released in 1994, but even for that time period it's very structurally innovative. The film is an anthology following the loosely-intertwined romantic lives of two heartbroken Chinese policemen, played by Takeshi Kaneshiro and Tony Leung. 

In Kaneshiro's story, his policeman, He Zhi Wu, is obsessively reeling from a break-up with his girlfriend, May, and ends up encountering a woman in a blonde wig (Brigitte Lin) who, unbeknownst to him, is involved in the Hong Kong crime underworld. Cop 663's (Leung) story follows a young woman, Faye (Faye Wong), who has fallen for a heartbroken police officer and, upon mistakenly obtaining his keys, lets herself in. She cleans his apartment and slowly improves his mood without him knowing. The two stories feature similar themes and plot events, but they're also romantic in surprising ways, making it an interesting film to watch if you're feeling like the two cops in "Chungking Express." 

It's safe to say that everybody has been through a break-up of some kind that has left them feeling like Robbie Hart from "The Wedding Singer." One of the best Adam Sandler movies, the 1998 film centers on a down-on-his-luck wedding singer in 1985 who finds himself falling in love with a waitress, played by Drew Barrymore in the first collaboration between the actress and the "Saturday Night Live" alum. While it's a very sweet film, much of the comedy comes from Sandler's petulant heartbreak, best evidenced by the song he sings to Barrymore's character about his ex-fiancée. 

What makes "The Wedding Singer" such a great post-break-up movie is the fact that it acknowledges that, as destructive as a break-up can be to someone, it's hard to convince even the most cynical person that love doesn't exist. As much as Sandler's character is in the pits of despair after being stood up at the altar, resisting the urge to fall for Barrymore's character is simply impossible. It's a good thing they all live happily ever after, or else those who have broken up with someone might lose hope after watching the film. 

Even though he's widely known for eclectic comedic films like "Dumb and Dumber" and "Bruce Almighty," some of the best Jim Carrey movies feature the actor's dramatic work, with the most obvious example of this being the 2004 surrealist drama "Eternal Sunshine of the Spotless Mind." Written by Charlie Kaufman, Carrey stars as Joel, a man reeling from his break-up with Clementine (Kate Winslet), only to discover she has paid for a highly-experimental procedure to erase her memories of him, convincing Joel to do the same, which forces him to re-experience all his memories with from end to beginning.

Famously, "Eternal Sunshine of the Spotless Mind" has an ambiguous ending that reveals how, despite the procedures seemingly working on both Clementine and Joel, they are nevertheless drawn to each other once again. It's a lot more hopeful and romantic of an ending than some of these other films we're looking at, but don't run away with any ideas that a break-up is always a bad idea. Perhaps for those of you reading going through a separation, you'll be better off without needing any procedures to eradicate your ex from your memory. 

One of the most iconic comedy films of the 2000s is "Forgetting Sarah Marshall," directed by Nicholas Stoller and written by Jason Segel. Segel stars as Peter, a television composer whose girlfriend, actress Sarah Marshall (Kristen Bell), suddenly dumps him. In an attempt to get over his heartbreak, he books a solo vacation to Hawaii, where he ends up bumping into Sarah and her new boyfriend, rock star Aldous Snow (Russell Brand). It's a film that sinks its teeth into a sucky relationship as Peter is forced to move on under absurd circumstances, but it's also a surprisingly heartfelt rom-com.

In particular, Peter's heartbreak is remedied when he meets Rachel (Mila Kunis), an employee at the resort where he and Sarah happen to be staying. Their burgeoning romance begins to blossom in competition with that of Sarah and Aldous, resulting in an extremely cathartic ending in which Peter is forced to choose between the two women, and opts for the one who hasn't broken his heart. If you want a break-up movie that's as sweet as it is raunchy, "Forgetting Sarah Marshall" is a classic you should definitely watch, or re-watch if you've already seen it. 

Okay, time for some break-up movies that'll guarantee an existential crisis. "(500) Days of Summer" seems, on the surface, like a typical rom-com following the short-lived relationship between Tom Hansen (Joseph Gordon-Levitt) and Summer Finn (Zooey Deschanel). However, it's also told out of sequence, and in its depiction of a seemingly happy relationship that actually wasn't all it's cracked up to be, it's become one of the most analyzed and talked-about romances in modern film.

In case you need a reminder of how rose-colored glasses can often blind us to red flags and signs that love was starting to fade (which, if you've been recently broken up with, you probably don't), "(500) Days of Summer" is a beautiful film that reminds us how relationships may just end up being moments in time, but can make us all the better for having experienced them. Of course, there are plenty of people who think that Tom is a male manipulator, but let's just chalk that up to people's own interpretations. 

Let's step away from the world of comedy to explore a break-up movie that is about as dramatic as it gets. "Blue Valentine," directed by Derek Cianfrance, was released in 2010 and caused quite a stir at the time after the MPAA gave it an NC-17 rating for an explicit scene involving oral sex. However, people who were pressed about that missed the real juice of the film, which tells the story of a marriage between Dean (Ryan Gosling) and Cindy (Michelle Williams), jumping back and forth between their college-aged courtship and their sad married life years later. 

If you're in the mood for a film with a happy ending, this is not the one for you. Everything about this film is deeply sad, from the doomed relationship between Dean and Cindy, to even its making-of in 2009, in which Williams was still recovering from the death of her partner, Heath Ledger, in 2008. "Blue Valentine" is an extremely difficult watch, whether you've experienced a split like this or not, but it might be the exact kind of catharsis you need after dealing with a heartbreak. 

Okay, now for something a little lighter: A rom-com starring Andy Samberg and Rashida Jones. "Celeste and Jesse Forever" was written by Jones and her writing partner Will McCormack and directed by Lee Toland Krieger, following a married couple who divorce with the promise to remain friends, which goes about as well as you'd expect from exes. As Jesse (Samberg) begins to move on in a new relationship, Celeste (Jones) has second thoughts about their separation and finds herself struggling to get back out into the dating pool.

The film finds Rashida Jones making herself the leading lady she deserves to be, and features a surprisingly great performance from Samberg as well. The film's supporting cast is also stacked with talent like Elijah Wood and Emma Roberts, but as far as break-up movies go, "Celeste and Jesse Forever" explores the difficulties of ending a marriage while also keeping things light and exploring the positives as much as the negatives. It's a lot less raunchy than, say, "Forgetting Sarah Marshall," though it also stars a third of the Lonely Island, so you can expect some dirty jokes here and there. 

We've been talking a lot about romantic break-ups, but those aren't the only ones that can affect a person's mental health. Take, for instance, "Frances Ha," a 2012 comedy directed by Noah Baumbach and co-written by and starring Greta Gerwig. Gerwig plays the titular Frances Halladay (the title refers to her last name not fitting her apartment's mailbox), a dancer who is forced to move out of the Brooklyn apartment she shares with her best friend, Sophie (Mickey Summer), resulting in them growing apart as Frances must find a new place to live.

Not only does "Frances Ha" have one of the best movie soundtracks of the 2010s, but it feels very slice-of-life and intricate in how Frances grieves her friendship that's not gone but also isn't really there. It also features the relatable early-20s struggle of your best friend getting into a relationship, and how that can create obstacles for two people who are so used to spending all their time together. It's a film that's so good, it makes you wonder why Gerwig isn't in front of the camera more often these days, despite having a thriving career as the director of "Lady Bird" and "Barbie."

What is there to say about this movie that hasn't already been said in light of the film's incredible longevity and relevance in modern film? Damien Chazelle's 2017 masterpiece stars Emma Stone as Mia, an aspiring actress who moves to Los Angeles and sparks a romance with Sebastian, a jazz pianist moonlighting in an amateur cover band. Stone and Gosling sparkle in "La La Land," a musical that pays tribute to the Golden Age of Hollywood, whilst simultaneously tearing down the lavish grandiosity that can entice so many people to move to Los Angeles.

That's best exemplified by the film's central relationship, which hits a roadblock when Sebastian agrees to tour with his pop band while Mia's one-woman play bombs. While there's obviously love between the two by the end, they must go their separate ways in order to fulfill their dreams, which, by the movie's heart-wrenching ending, seems to be the case. It's a movie that is as magnificent to watch as it is to feel, which is everything you want in a break-up movie. Plus, you get to see the performance that won Emma Stone her first (but not her last) Oscar for Best Actress. 

You probably missed "Someone Great" when it released on Netflix in 2019, but it definitely deserves your attention as one of the best break-up movies in recent years. Gina Rodriguez stars as Jenny, a woman whose long-term relationship with her college boyfriend, Nate (LaKeith Stanfield), ends over her impending move across the country. She decides to spend her last night in New York City partying with her girlfriends, Erin (DeWanda Wise) and Blair (Brittany Snow), all the while with the film flashing back through Jenny and Nate's relationship through its highs and lows.

Not only does "Someone Great" include one of the best cinematic needle drops of 2019 in "Truth Hurts" by Lizzo, which underscores Jenny dancing around her apartment in her underwear. Taylor Swift also cited the film as an inspiration for her song "Death By A Thousand Cuts." If that doesn't convince you that "Someone Great" is the tear-jerking break-up movie you need to watch next, I don't know what will.

You've probably seen the memes hundreds of times by now, but don't forget that "Marriage Story" is also one of the most brutal depictions of divorce we've seen in a movie to date. Scarlett Johansson and Adam Driver dazzle in Noah Baumbach's heartfelt drama, in which the amicable separation between actress Nicole (Johansson) and theater director Charlie (Driver) turns ugly as their respective lawyers (including an Oscar-winning performance from Laura Dern) dredge up old conflicts and unhealed wounds between the two parents. 

It's an incredibly brutal, albeit realistic portrayal, of what a divorce between two people trying to keep things together for their shared child looks like. It's obviously now famous for an endlessly-replayed climactic scene in which Nicole and Charlie argue and insult each other, but if you're watching the film as it's meant to be seen, it'll give you chills. This is the type of film you watch when you want to be reminded that, even if your own break-up seems devastating, it could always be worse. 

Thank God for "The Worst Person in the World," because without it, we may not have the currently thriving career of Norwegian actress Renate Reinsve. As Reinsve told /Film about how "The Worst Person in the World" changed her life, "I didn't know really how to do this role because she was so complex, and that's very rare." Released in 2021 and directed by Joachim Trier, the film follows the life of Julie, a woman who breaks up with her long-term boyfriend Aksel (Anders Danielsen Lie) just as she turns 30, only for him to later be diagnosed with terminal cancer. 

This wistful, anti-romantic comedy might be a break-up film, but it's also a deep character study about Julie, whom Reinsve plays with such empathy despite her actions in the film being quite regrettable. If there's any film from this list you should immediately go watch, it's this one, because no other film captures the confusing and oftentimes contradictory reasoning behind a break-up. Plus, it'll get you excited for Trier's follow-up this year, which Reinsve also stars in. 

On a similar note to "Frances Ha," "The Banshees of Inisherin" is one of the most brutal break-up movies ever made, which is to be expected from a director like Martin McDonagh, whose previous works include "In Bruges" and "Three Billboards Outside Ebbing, Missouri." Set on an Irish island in 1923, Brendan Gleeson stars as Colm, a man who abruptly ends his friendship with Pádraic (Colin Farrell), citing his desire to be remembered before he dies. However, Pádraic's attempts to win back Colm's affection turn morbid as both of their lives proceed to spiral out of control.

The film also features two outstanding supporting performances in Kerry Condon, who plays Pádraic's sister Siobhán, as well as Barry Keoghan as Dominic, a mentally handicapped teenager who is Pádraic's only other friend. Despite being incredibly funny from time to time, "The Banshees of Inisherin" is also incredibly sad, as Pádraic's attempts to deal with the aftermath of his friendship ending cause chaos for the other islanders, particularly Colm, who is so determined to keep Pádraic away that he begins to cut off his own fingers. Let's just be glad none of us has done anything like that over a break-up.