Watchworthy

The Best Movies About Breakups

Updated February 14, 2020 3.4k votes 446 voters 17.7k views 37 items

List Rules Films about break ups, divorces, and even splits between friends

There’s almost nothing that will make you feel better about being dumped or being, well single than watching a great movie about breaking up. Let’s face it – some of the movies on this list are great, but won’t go down in history as being the best of all time; others have actually become classics in the film industry. In any case, they're all about characters going through a break up.

The movies that are featured on this list span multiple genres – some are inspiring, some are completely dramatic, others are emotionally devastating, and the rest are comedies (though some are funnier than others).

This list has the best movies about breakups, including: Breaking Upwards, Annie Hall, Kramer Vs. Kramer, Eternal Sunshine of the Spotless Mind, Sliding Doors, Great Expectations, and High Fidelity.

Vote up your favorite movie below, vote down the film you wish you could break up with, or add a favorite that isn't already on the list.

Data-driven recommendations based on voting from over 40 million monthly visits to Ranker. Try the free app

list ordered by

Forgetting Sarah Marshall Mila Kunis, Kristen Bell, Russell Brand

Released: 2008

Directed by: Nicholas Stoller

Forgetting Sarah Marshall is a 2008 American romantic comedy-drama film directed by Nicholas Stoller and starring Jason Segel, Kristen Bell, Mila Kunis and Russell Brand. The film, which was ...more

The Wedding Singer is listed (or ranked) 2 on the list The Best Movies About Breakups

The Wedding Singer Drew Barrymore, Adam Sandler, Steve Buscemi

Released: 1998

Directed by: Frank Coraci

The Wedding Singer is a 1998 romantic comedy film written by Tim Herlihy and directed by Frank Coraci. It stars Adam Sandler as a wedding singer in the 1980s and Drew Barrymore as a waitress ...more

Eternal Sunshine of the ... is listed (or ranked) 3 on the list The Best Movies About Breakups

Eternal Sunshine of the Spotless Mind Kate Winslet, Kirsten Dunst, Jim Carrey

Released: 2004

Directed by: Michel Gondry

Eternal Sunshine of the Spotless Mind is a 2004 American romantic science-fiction comedy-drama film about an estranged couple who have each other erased from their memories, written by Charlie ...more

The Break-Up Vince Vaughn, Jennifer Aniston, Ann-Margret

Released: 2006

Directed by: Peyton Reed

The Break-Up is a 2006 American romantic comedy-drama film directed by Peyton Reed. In a bid to keep their luxurious condo from their significant other, a newly broken up couple (Vince Vaughn ...more

(500) Days of Summer Zooey Deschanel, Minka Kelly, Chloë Grace Moretz

Released: 2009

Directed by: Marc Webb

(500) Days of Summer is a 2009 American romantic comedy-drama film by first time director Marc Webb. On January 8, Tom Hansen (Joseph Gordon-Levitt) meets Summer Finn (Zooey Deschanel), his ...more

Chasing Amy Ben Affleck, Matt Damon, Kevin Smith

Released: 1997

Directed by: Kevin Smith

Chasing Amy is a 1997 American romantic comedy film written and directed by Kevin Smith. The central tension revolves around sexuality, sexual history, and evolving friendships. It is the third ...more

The War of the Roses Kathleen Turner, Danny DeVito, Michael Douglas

Released: 1989

Directed by: Danny DeVito, Thomas Lofaro

This film is a 1989 American black comedy film based upon the 1981 novel of the same name by Warren Adler. The film follows a wealthy couple with a seemingly perfect marriage. When their ...more

Kramer vs. Kramer Meryl Streep, Dustin Hoffman, JoBeth Williams

Released: 1979

Directed by: Robert Benton

Kramer vs. Kramer is a 1979 American drama film adapted by Robert Benton from the novel by Avery Corman, and directed by Benton. The film tells the story of a married couple's divorce and its ...more

The Breaker Upperers is listed (or ranked) 9 on the list The Best Movies About Breakups

The Breaker Upperers Madeleine Sami, Jackie van Beek, James Rolleston

Released: 2019

Directed by: Madeleine Sami, Jackie van Beek

The Breaker Upperers is a 2018 New Zealand romantic-comedy film that was written, directed and starring Madeleine Sami and Jackie van Beek. Two women, Mel (Madeleine Sami) and Jen (Jackie van ...more

High Fidelity is listed (or ranked) 10 on the list The Best Movies About Breakups

High Fidelity Catherine Zeta-Jones, Bruce Springsteen, Jack Black

Released: 2000

Directed by: Stephen Frears

High Fidelity is a 2000 American comedy-drama film directed by Stephen Frears and starring John Cusack and Iben Hjejle. The film is based on the 1995 British novel of the same name by Nick ...more

Tom Islava added The Odd Couple Jack Lemmon, Walter Matthau, Herb Edelman

Released: 1968

Directed by: Gene Saks

The Odd Couple is a 1968 American black comedy film written by Neil Simon, based on his play The Odd Couple, directed by Gene Saks, and starring Jack Lemmon and Walter Matthau. It is the story ...more

Annie Hall Woody Allen, Diane Keaton, Sigourney Weaver

Released: 1977

Directed by: Woody Allen

Annie Hall is a 1977 American romantic comedy film directed by Woody Allen. Neurotic New York comedian Alvy Singer (Allen) falls in love with the ditzy Annie Hall (Diane Keaton).

Swingers Heather Graham, Vince Vaughn, Jon Favreau filmography

Released: 1996

Directed by: Doug Liman

This film is a 1996 comedy-drama film about the lives of single, unemployed actors living on the 'eastside' of Hollywood, California during the 1990s swing revival. Written by Jon Favreau and ...more

Closer Natalie Portman, Julia Roberts, Jude Law

Released: 2004

Directed by: Mike Nichols

Closer is a 2004 romantic drama film written by Patrick Marber, based on his award-winning 1997 play of the same name. The movie was produced and directed by Mike Nichols and stars Julia ...more

She-Devil Meryl Streep, Roseanne Barr, Linda Hunt

Released: 1989

Directed by: Susan Seidelman

She-Devil is a 1989 American dark comedy film directed by Susan Seidelman and written by Barry Strugatz and Mark R. Burns. It stars Meryl Streep, Ed Begley, Jr. and Roseanne Barr in her film ...more

Wuthering Heights Laurence Olivier, David Niven, Merle Oberon

Released: 1939

Directed by: William Wyler

Wuthering Heights is a 1939 American black-and-white film directed by William Wyler and produced by Samuel Goldwyn. It is based on the novel, Wuthering Heights by Emily Brontë. The film ...more

Tom Islava added Midnight in Paris Rachel McAdams, Marion Cotillard, Tom Hiddleston

Released: 2011

Directed by: Woody Allen

Midnight in Paris is an American 2011 romantic comedy fantasy film written and directed by Woody Allen. Set in Paris, the film follows Gil Pender, a screenwriter, who is forced to confront the ...more

The Way We Were Barbra Streisand, Robert Redford, James Woods

Released: 1973

Directed by: Sydney Pollack

The Way We Were is a 1973 American romantic drama film, starring Barbra Streisand and Robert Redford, and directed by Sydney Pollack. The screenplay by Arthur Laurents was based on his college ...more

Marriage Story is listed (or ranked) 19 on the list The Best Movies About Breakups

Marriage Story Adam Driver, Scarlett Johansson, Laura Dern

Released: 2019

Directed by: Noah Baumbach

Marriage Story is a 2019 American drama film directed by Noah Baumbach. A stage director (Adam Driver) and his actor wife (Scarlett Johansson) struggle through a grueling, coast-to-coast divorce ...more

After Midnight Jeremy Gardner, Brea Grant, Justin Benson

Released: 2020

Directed by: Jeremy Gardner

After Midnight is a 2020 American romantic monster movie directed by Jeremy Gardner and Christian Stella. Hank (Jeremy Gardner) discovers his long time girlfriend (Brea Grant) has left town as ...more

The Story of Us Michelle Pfeiffer, Bruce Willis, Betty White

Released: 1999

Directed by: Rob Reiner

The Story of Us is a 1999 American romantic comedy drama film directed by Rob Reiner, and starring Bruce Willis and Michelle Pfeiffer as a couple married for 15 years. The depiction of the ...more

Tone-Deaf is listed (or ranked) 22 on the list The Best Movies About Breakups

Tone-Deaf Amanda Crew, Robert Patrick, Hayley Marie Norman

Released: 2019

Directed by: Richard Bates Jr.

Tone-Deaf is a 2019 American comedy horror film directed by Richard Bates Jr. After losing her job and reaching the end of a complicated relationship, a woman rents a country house from a ...more

Great Expectations Gwyneth Paltrow, Robert De Niro, Ethan Hawke

Released: 1998

Directed by: Alfonso Cuarón

Great Expectations is a 1998 contemporary film adaptation of the Charles Dickens novel of the same name, co-written and directed by Alfonso Cuarón and starring Ethan Hawke, Gwyneth ...more

The Last Five Years is listed (or ranked) 24 on the list The Best Movies About Breakups

DeborahTragasz added The Last Five Years Anna Kendrick, Sherie Rene Scott, Jeremy Jordan

Released: 2014

Directed by: Richard LaGravenese

The Last 5 Years is an upcoming American musical comedy-drama film written and directed by Richard LaGravenese. The film stars Anna Kendrick and Jeremy Jordan. The film is based on Jason Robert ...more

The Upside of Anger Evan Rachel Wood, Kevin Costner, Keri Russell

Released: 2005

Directed by: Mike Binder

The Upside of Anger is a 2005 American romantic comedy and drama film written and directed by Mike Binder and set in Bloomfield Hills, Michigan. It stars Joan Allen, Kevin Costner and Evan ...more