Breaking up is hard to do. The adage is true, and while the breakups featured in these films are painful, they are also interesting and entertaining for audiences. The powerful fracturing of unions reminds us of some of our own heartaches.

Stacker dug into the rich history of break-up cinema and made a list of the best movies across genres and over the decades. From movies following people in the traumatic aftermath of a behind-the-scenes split to those with pivotal break-up scenes and others with multiple breakups strewn throughout—the films on this list all illustrate narrative-defining break-up moments. To qualify, the film had to have at least a 6.5 on IMDb and over 2,000 user votes. Metascores were also provided for critical context.

These films cross genres and feature characters from all walks of life. One movie focuses on the breakdown of a marriage and how far a couple will go to hold onto the marital home. Another finds a middle-aged New Yorker redefining her life and identity after discovering her husband’s extramarital affairs.

Keep reading to see if your favorite break-up movie made the list.

(500) Days of Summer (2009)

Fox Searchlight Pictures

– Director: Marc Webb
– IMDb user rating: 7.6
– Metascore: 76
– Runtime: 95 minutes

After being dumped by the woman he believes he was meant to be with, Tom reexamines their relationship so he can figure out what happened and try to get her back. The film, starring Zooey Deschanel as Summer and Joseph Gordon-Levitt as Tom, was nominated for two Golden Globes, including best motion picture in a comedy or musical and best performance by an actor in a motion picture comedy or musical for Gordon-Levitt.
A Separation (2011)

Asghar Farhadi Productions

– Director: Asghar Farhadi
– IMDb user rating: 8.3
– Metascore: 95
– Runtime: 123 minutes

Simin wants to leave Iran with her daughter to provide her with a better life, but her husband Nader wants to stay to care for his father, who has Alzheimer’s. When Simin leaves to stay with her mother and sues for divorce, Nader remains at their home. He hires a woman to take care of his father, and things go horribly wrong. “A Separation” became the first Iranian film to win an Oscar when it snagged an Academy Award for best foreign language film in 2011.
An Unmarried Woman (1978)

Major Studio Partners

– Director: Paul Mazursky
– IMDb user rating: 7.2
– Metascore: 79
– Runtime: 124 minutes

Jill Clayburgh plays Erica, a comfortable Manhattanite whose husband leaves her for another woman. Alone, Erica rediscovers who she is as she stumbles through ladies’ night, single parenthood, dating, a love affair, and a return to the working world. The film received a Best Picture Oscar nomination as did Clayburgh for best actress in a leading role.
Asako I & II (2018)

Bitters End

– Director: Ryûsuke Hamaguchi
– IMDb user rating: 6.9
– Metascore: 68
– Runtime: 119 minutes

Asako, a young woman in Osaka, meets and falls in love with the mysterious, free-spirited Baku. The relationship does not last, and Asako eventually meets another man who looks like Baku but has a very different personality. In the end, Asako must decide which of the men she wants to be with.
The Awful Truth (1937)

Columbia Pictures

– Director: Leo McCarey
– IMDb user rating: 7.7
– Metascore: 87
– Runtime: 90 minutes

A married couple, played by Cary Grant and Irene Dunne, suspect infidelity in their union and agree to divorce. They each strike up new romantic relationships before realizing how much they still love each other. This classic rom-com finds them both trying to jeopardize the other’s newfound relationship.
Blue Valentine (2010)

Incentive Filmed Entertainment

– Director: Derek Cianfrance
– IMDb user rating: 7.3
– Metascore: 81
– Runtime: 112 minutes

This film tells the tale of married couple Dean and Cindy, who examine their past and present to discover where they are and how they got there. Michelle Williams, who received an Oscar nod for her performance, and Ryan Gosling, portray the couple as they journey through the beginning of their relationship, their marriage, and the birth of their daughter, Frankie. While Gosling’s character seems fine with the marriage as it is, Williams’ character seems stuck and wanting more.
Casablanca (1942)

Warner Bros.

– Director: Michael Curtiz
– IMDb user rating: 8.5
– Metascore: 100
– Runtime: 102 minutes

In a desperate attempt to flee Nazi-occupied Morocco with her husband, Ilsa (Ingrid Bergman) seeks the help of her former lover, Rick (Humphrey Bogart), who begrudgingly obliges to see them to safety. Regarded as one of the best pictures in film history, this Michael Curtiz-directed classic took home three of the eight Academy Awards for which it was nominated in 1942, including best picture and best director.
Forgetting Sarah Marshall (2008)

Universal Pictures

– Director: Nicholas Stoller
– IMDb user rating: 7.1
– Metascore: 67
– Runtime: 111 minutes

Jason Segel stars as a lovelorn and dumped man who goes to Hawaii on vacation to get away and forget his actress ex-girlfriend, played by Kristen Bell. Unfortunately, she winds up at the same resort with her new boyfriend in tow. Mila Kunis, Bill Hader, Russell Brand, Paul Rudd, and Jonah Hill also star in this comedy film written by Segel.
Happy Together (1997)

Block 2 Pictures

– Director: Wong Kar-wai
– IMDb user rating: 7.7
– Metascore: 70
– Runtime: 96 minutes

Two gay men from Hong Kong, Lai and Ho, travel to Argentina to mend their broken relationship, but they eventually go their separate ways. Lai works as a doorman and Ho works as a hooker, with the former taking care of the latter after he gets beat up. This brings them back into each other’s lives though they do not return to a romantic relationship, and by the end of the film, Lai leaves Argentina for home, leaving Ho behind.
Her (2013)

Annapurna Pictures

– Director: Spike Jonze
– IMDb user rating: 8.0
– Metascore: 91
– Runtime: 126 minutes

After a failed marriage, Theodore Twombly (Joaquin Phoenix) starts up a romance with Samantha, his operating system, but things get complicated. Voiced by Scarlett Johansson, Samantha ultimately reveals that she loves many men she connects with, leaving Theodore to contemplate how difficult modern love is. The Oscar-winning film also stars Rooney Mara and Amy Adams.
High Fidelity (2000)

Touchstone Pictures

– Director: Stephen Frears
– IMDb user rating: 7.5
– Metascore: 79
– Runtime: 113 minutes

John Cusack plays Rob, a disaffected record store owner whose girlfriend dumps him because he refuses to change. He then examines his top five breakups and tracks down the women to see what he continues to do wrong in the romance department. Zoë Kravitz, whose mother Lisa Bonet appeared in the original 2000 film, starred in Hulu’s 2020 TV series version of “High Fidelity,” where she takes over the role of Rob.
Journey to Italy (1954)

Italia Film

– Director: Roberto Rossellini
– IMDb user rating: 7.3
– Metascore: 100
– Runtime: 97 minutes

After eight years of marriage, Katherine and Alex Joyce begin to question how well they know each other and whether their marriage is salvageable on a trip to Italy. The journey is a revelatory one; just as they decide to divorce, a religious procession and a remarkable afternoon together convince them of their love for one another. Ingrid Bergman, who plays Katherine, had a scandalous affair with director Roberto Rossellini, which led to marriage and, eventually, divorce.
Kill Bill: Volume 2 (2004)

Miramax

– Director: Quentin Tarantino
– IMDb user rating: 8.0
– Metascore: 83
– Runtime: 137 minutes

In this action-packed sequel, the Bride (Uma Thurman) not only continues to seek vengeance against ex-lover Bill, but she sets her sights on those who betrayed her years before, including Bill’s brother Budd and Elle Driver. She will have her confrontation with the man who attempted to have her killed at her wedding in this follow-up to “Kill Bill: Volume 1.” While it has yet to be confirmed, fans could be receiving another installment in the “Kill Bill” franchise.
The Last Picture Show (1971)

Columbia Pictures

– Director: Peter Bogdanovich
– IMDb user rating: 8.0
– Metascore: 93
– Runtime: 118 minutes

Duane, a local high schooler in a dying Texas town, dates the most beautiful girl around, Jacy, while his friend Sonny breaks up with his girlfriend and has an affair with an older woman. This coming-of-age film featured Cybill Shepherd in her first film role as the beautiful Jacy, who eventually breaks up with Duane and marries Sonny. Peter Bogdanovich released a sequel to the film in 1990 called “Texasville.”
Medicine for Melancholy (2008)

Strike Anywhere

– Director: Barry Jenkins
– IMDb user rating: 6.7
– Metascore: 62
– Runtime: 88 minutes

Micah and Jo have a one-night stand and wake up together the following morning. The couple spends the day together getting to know each other, and they realize that they are very different. In the end, the characters go their separate ways in this film that marks director Academy Award-winning director Barry Jenkins’ feature film debut.
Midsommar (2019)

A24

– Director: Ari Aster
– IMDb user rating: 7.1
– Metascore: 72
– Runtime: 148 minutes

Young couple Dani and Christian’s relationship almost ended, but a tragedy brought them closer together. They travel to a Swedish village to help Dani process her grief and celebrate a midsummer festival, but things grow increasingly strange and violent in this mind-bending film.
Mrs. Doubtfire (1993)

Twentieth Century Fox

– Director: Chris Columbus
– IMDb user rating: 7.0
– Metascore: 53
– Runtime: 125 minutes

To spend more time with his kids after his divorce, unemployed actor Daniel Hillard (Robin Williams) takes on the role of a lifetime as Mrs. Doubtfire, an elderly woman who eventually winds up nannying for his kids. As the affable Englishwoman, he gets to know his ex-wife’s new boyfriend, played by Pierce Brosnan, which is incredibly awkward and funny.
Paris, Texas (1984)

Road Movies Filmproduktion

– Director: Wim Wenders
– IMDb user rating: 8.1
– Metascore: 78
– Runtime: 145 minutes

Travis (Harry Dean Stanton) walks out of the desert years after he went missing to pick up the pieces of a marriage and family he ruined with his jealousy and drinking. He rediscovers his relationship with his son, who now lives with Travis’ brother and wife, but Travis is determined to find his wife, Jane (Nastassja Kinski), and reunite mother and son. After Travis wandered away, Jane left their son and became a sex worker in Texas.
Scenes from a Marriage (1974)

Cinematograph AB

– Director: Ingmar Bergman
– IMDb user rating: 8.4
– Metascore: data not available
– Runtime: 169 minutes

This film documents the many phases of love as Marianne (Liv Ullmann) and Johan (Erland Josephson) marry, face infidelity, decide to divorce, and partner with other people. The film was based on a 1973 miniseries, which was also written and directed by Ingmar Bergman, and was remade as a miniseries for HBO in 2021 with Jessica Chastain and Oscar Isaac as the title characters. Bergman’s son, Daniel, acted as an executive producer.
Swingers (1996)

Doug Liman Productions

– Director: Doug Liman
– IMDb user rating: 7.2
– Metascore: 71
– Runtime: 96 minutes

Jon Favreau wrote “Swingers” and starred as Mike, a man whose relationship has ended. Mike can’t seem to move on, so his friends try to get him back into the swing of things by journeying out into the Los Angeles social scene. Heather Graham, Vince Vaughn, and Ron Livingston also star in the film loosely based on Favreau’s own experiences.
Three Colors: White (1994)

MK2 Productions

– Director: Krzysztof Kieślowski
– IMDb user rating: 7.6
– Metascore: 88
– Runtime: 92 minutes

Ashamed, jobless, and devastated by the outcome of a divorce that leaves him with next to nothing to his name, a Polish hairdresser named Karol (Zbigniew Zamachowski) hatches a scheme to get payback on his French wife Dominique (Julie Delpy). Despite failing to secure an Oscar nomination for best foreign language film at the 67th Academy Awards, the second chapter of Krzysztof Kieślowski’s “Three Colours” trilogy earned the Polish film director the coveted Silver Bear for best director at the 1994 Berlin International Film Festival.
The War of the Roses (1989)

Twentieth Century Fox

– Director: Danny DeVito
– IMDb user rating: 6.8
– Metascore: 79
– Runtime: 116 minutes

Kathleen Turner and Michael Douglas play a wealthy married couple, the Roses. When their marriage falls apart, they refuse to leave their marital home and find unbelievable and dangerous ways to force the other one out. Director Danny DeVito also stars as divorce attorney Gavin D’Amato, who narrates the tale as it unfolds.
The Way We Were (1973)

Columbia Pictures

– Director: Sydney Pollack
– IMDb user rating: 7.1
– Metascore: 61
– Runtime: 118 minutes

Starring Barbra Streisand and Robert Redford, “The Way We Were” follows a couple as they navigate through decades as friends and lovers though they have fundamentally different backgrounds and views on life, which ultimately tear them apart. The film won two Oscars for best music, original dramatic score and best music, original song for “The Way We Were.”
Women on the Verge of a Nervous Breakdown (1988)

Laurenfilm

– Director: Pedro Almodóvar
– IMDb user rating: 7.6
– Metascore: 85
– Runtime: 88 minutes

Pepa Marcos goes on a journey to find the lover who left her and find out why. She meets a strange cast of characters, including her lover’s son and wife. Carmen Maura, who played Pepa, had a falling out with the film’s director, Pedro Almodóvar, and they didn’t work together until she acted in his 2006 film “Volver.”
The Worst Person in the World (2021)

Oslo Pictures

– Director: Joachim Trier
– IMDb user rating: 8.0
– Metascore: 89
– Runtime: 127 minutes

The film’s protagonist, Julie, contemplates breaking up with her decade-older boyfriend, Aksel, as she tries to navigate life changes and falls for another guy. “The Worst Person in the World” follows Julie over several years and is the third film in director Joachim Trier’s “Oslo Trilogy.”