• Entertainment

The Best Movies About Breakups

List RulesFilms 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.
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  • 1
    Mila Kunis, Kristen Bell
    143
    42

    Released2008

    Directed byNicholas 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 written  ...more
  • 2
    Adam Sandler, Drew Barrymore
    124
    55

    Released1998

    Directed byFrank Coraci

    Set in 1985, Adam Sandler plays a nice guy with a broken heart who's stuck in one of the most romantic jobs in the world, a wedding singer. He loses all hope when he is abandoned at the altar by his  ...more
  • 3
    Kate Winslet, Kirsten Dunst
    96
    43

    Released2004

    Directed byMichel 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
  • 4
    Vince Vaughn, Jennifer Aniston
    89
    51

    Released2006

    Directed byPeyton Reed

    When Brooke (Jennifer Aniston), an art dealer, and Gary (Vince Vaughn), a tour-bus driver, finally call it quits in their relationship, neither is willing to move out of their shared condo. With  ...more
  • 5
    Joseph Gordon-Levitt, Zooey Deschanel
    84
    51

    Released2009

    Directed byMarc Webb

    Tom (Joseph Gordon-Levitt), greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer (Zooey Deschanel), suddenly dumps him. He reflects on their 500 days  ...more
  • 6
    Michael Douglas, Kathleen Turner
    65
    43

    Released1989

    Directed byDanny DeVito

    After 17 years of marriage, Barbara (Kathleen Turner) and Oliver Rose (Michael Douglas) want out. The trouble is, neither one wants to part with their opulent home. So begins a long war between  ...more
  • 7
    Ben Affleck, Joey Lauren Adams
    61
    39

    Released1997

    Directed byKevin Smith

    Holden and Banky are best friends and authors of a popular comic book. Holden falls in love with Alyssa, who happens to be a lesbian. Holden's relationship with Alyssa strains his life-long  ...more
  • 8
    Madeleine Sami, Jackie van Beek
    73
    54

    Released2019

    Directed byMadeleine 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 Beek)  ...more
  • 9
    Meryl Streep, Dustin Hoffman
    51
    34

    Released1979

    Directed byRobert 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 impact  ...more
  • 10
    Tom Islava addedJack Lemmon, Walter Matthau
    21
    7

    Released1968

    Directed byGene Saks

    When fussy Felix (Jack Lemmon) becomes suicidal over his impending divorce, he accepts an offer to move in with his best friend, messy Oscar (Walter Matthau). Felix drives Oscar crazy with his  ...more
  • 11
    John Cusack, Iben Hjejle
    49
    44

    Released2000

    Directed byStephen Frears

    Rob Gordon (John Cusack) is the owner of a failing record store in Chicago, where he sells music the old-fashioned way -- on vinyl. Although they have an encyclopedic knowledge of pop music and are  ...more
  • 12
    Adam Driver, Scarlett Johansson
    9
    3

    Released2019

    Directed byNoah 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 that  ...more
  • 13
    Meryl Streep, Roseanne Barr
    37
    48

    Released1989

    Directed bySusan Seidelman

    Housewife and mother Ruth Patchett (Roseanne Barr), an overweight and unkempt woman, can seem to do nothing to make her husband, Bob (Ed Begley Jr.), happy. When he becomes embroiled in an affair  ...more
  • 14
    Woody Allen, Diane Keaton
    35
    47

    Released1977

    Directed byWoody Allen

    Comedian Alvy Singer (Woody Allen) examines the rise and fall of his relationship with struggling nightclub singer Annie Hall (Diane Keaton). Speaking directly to the audience in front of a bare  ...more
  • 15
    Merle Oberon, Laurence Olivier
    29
    41

    Released1939

    Directed byWilliam Wyler

    In this adaptation of the classic Emily Bronte novel set in 19th-century England, wealthy young Cathy Earnshaw (Merle Oberon) shares a loving bond with Heathcliff (Laurence Olivier), a poor childhood  ...more
  • 16
    Julia Roberts, Jude Law
    32
    45

    Released2004

    Directed byMike Nichols

    Alice (Natalie Portman), an American stripper who has moved to London, meets Dan (Jude Law) on the street. While looking at him, a taxi hits her. After taking her to the hospital, Dan begins dating  ...more
  • 17
    Jon Favreau, Vince Vaughn
    32
    46

    Released1996

    Directed byDoug Liman

    A transplanted New Yorker attempting to acclimate to Los Angeles, Mike Peters (Jon Favreau), is struggling to both boost his comedy career and get over his last relationship. A self-proclaimed master  ...more
  • 18
    Tom Islava addedOwen Wilson, Rachel McAdams
    10
    15

    Released2011

    Directed byWoody Allen

    Gil Pender (Owen Wilson) is a screenwriter and aspiring novelist. Vacationing in Paris with his fiancee (Rachel McAdams), he has taken to touring the city alone. On one such late-night excursion, Gil  ...more
  • 19
    Barbra Streisand, Robert Redford
    29
    45

    Released1973

    Directed bySydney Pollack

    Opposites attract when, during their college days, Katie Morosky (Barbra Streisand), a politically active Jew, meets Hubbell Gardiner (Robert Redford), a feckless WASP. Years later, in the wake of  ...more
  • 20

    The Story of Us

    Michelle Pfeiffer, Bruce Willis
    23
    39

    Released1999

    Directed byRob 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 marriage  ...more
  • 21
    Ethan Hawke, Gwyneth Paltrow
    22
    44

    Released1998

    Directed byAlfonso Cuarón

    Loosely based on the Charles Dickens' classic novel, "Great Expectations" is a sensual tale of a young man's unforgettable passage into manhood, and the three individuals who will undeniably change  ...more
  • 22

    The Upside of Anger

    Joan Allen, Kevin Costner
    18
    36

    Released2005

    Directed byMike Binder

    After her husband runs off with his secretary, Terry Wolfmeyer (Joan Allen) is left to fend for herself -- and her four daughters (Keri Russell, Evan Rachel Wood, Erika Christensen, Alicia Witt). As
  • 23
    Gwyneth Paltrow, John Hannah
    19
    45

    Released1998

    Directed byPeter Howitt

    When Helen (Gwyneth Paltrow), a London ad executive, is fired from her job and rushes out to catch a train, two scenarios take place. In one, she gets on the train and comes home to find her  ...more
  • 24
    William Hurt, Albert Brooks
    17
    42

    Released1987

    Directed byJames L. Brooks

    Intelligent satire of American television news. A highly strung news producer finds herself strangely attracted to a vapid anchorman even through she loathes everything he personifies. To make  ...more
  • 25
    Jill Clayburgh, Alan Bates
    11
    37

    Released1978

    Directed byPaul Mazursky

    An attractive and well-to-do New Yorker, Erica Benton (Jill Clayburgh), finds her comfortable existence upended when her husband, Martin (Michael Murphy), ends their marriage and takes up with a  ...more
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List Rules: Films about break ups, divorces, and even splits between friends