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The Best Movies About Breakups

Updated September 3, 2020 2.8k votes 451 voters 17.9k views38 items

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
    Forgetting Sarah Marshall
    150
    45

    Forgetting Sarah Marshall

    Mila Kunis, Kristen Bell

    Released2008

    Directed byNicholas Stoller

    Forgetting Sarah Marshall is a 2008 American romantic comedy-drama film directed by Nicholas... more on Wikipedia
  • 2
    The Wedding Singer
    133
    56

    The Wedding Singer

    Drew Barrymore, Adam Sandler

    Released1998

    Directed byFrank Coraci

    The Wedding Singer is a 1998 romantic comedy film written by Tim Herlihy and directed by Frank... more on Wikipedia
  • 3
    Eternal Sunshine of the Spotless Mind
    100
    47

    Eternal Sunshine of the Spotless Mind

    Kate Winslet, Kirsten Dunst

    Released2004

    Directed byMichel Gondry

    Eternal Sunshine of the Spotless Mind is a 2004 American romantic science-fiction comedy-drama... more on Wikipedia
  • 4
    The Break-Up
    94
    54

    The Break-Up

    Vince Vaughn, Jennifer Aniston

    Released2006

    Directed byPeyton Reed

    The Break-Up is a 2006 American romantic comedy-drama film directed by Peyton Reed. In a bid... more on Wikipedia
  • 5
    (500) Days of Summer
    90
    55

    (500) Days of Summer

    Zooey Deschanel, Minka Kelly

    Released2009

    Directed byMarc Webb

    (500) Days of Summer is a 2009 American romantic comedy-drama film by first time director Marc... more on Wikipedia
  • 6
    The Breaker Upperers
    91
    65

    The Breaker Upperers

    Madeleine Sami, Jackie van Beek

    Released2019

    Directed byMadeleine Sami, Jackie van Beek

    The Breaker Upperers is a 2018 New Zealand romantic-comedy film that was written, directed and... more on Wikipedia
  • 7
    The War of the Roses
    70
    44

    The War of the Roses

    Kathleen Turner, Danny DeVito

    Released1989

    Directed byDanny DeVito, Thomas Lofaro

    This film is a 1989 American black comedy film based upon the 1981 novel of the same name by... more on Wikipedia
  • 8
    Chasing Amy
    64
    42

    Chasing Amy

    Ben Affleck, Matt Damon

    Released1997

    Directed byKevin Smith

    Chasing Amy is a 1997 American romantic comedy film written and directed by Kevin Smith. The... more on Wikipedia
  • 9
    The Odd Couple
    22
    9

    The Odd Couple

    Jack Lemmon, Walter Matthau

    Released1968

    Directed byGene Saks

    The Odd Couple is a 1968 American black comedy film written by Neil Simon, based on his play... more on Wikipedia
  • 10
    Sliding Doors
    55
    48

    Sliding Doors

    Gwyneth Paltrow, Jeanne Tripplehorn

    Released1998

    Directed byPeter Howitt

    Sliding Doors is a 1998 British-American romantic comedy-drama film written and directed by... more on Wikipedia
  • 11
    High Fidelity
    50
    43

    High Fidelity

    Catherine Zeta-Jones, Bruce Springsteen

    Released2000

    Directed byStephen Frears

    High Fidelity is a 2000 American comedy-drama film directed by Stephen Frears and starring... more on Wikipedia
  • 12
    An Unmarried Woman
    31
    38

    An Unmarried Woman

    Jill Clayburgh, Alan Bates

    Released1978

    Directed byPaul Mazursky

    An Unmarried Woman is a 1978 American comedy-drama film written and directed by Paul Mazursky,... more on Wikipedia
  • 13
    Marriage Story
    5
    2

    Marriage Story

    Adam Driver, Scarlett Johansson

    Released2019

    Directed byNoah Baumbach

    Marriage Story is a 2019 American drama film directed by Noah Baumbach. A stage director (Adam... more on Wikipedia
  • 14
    The Squid and the Whale
    30
    38

    The Squid and the Whale

    Anna Paquin, Alexandra Daddario

    Released2005

    Directed byNoah Baumbach

    The Squid and the Whale is a 2005 American arthouse comedy-drama film written and directed by... more on Wikipedia
  • 15
    Annie Hall
    35
    49

    Annie Hall

    Woody Allen, Diane Keaton

    Released1977

    Directed byWoody Allen

    Annie Hall is a 1977 American romantic comedy film directed by Woody Allen. Neurotic New York... more on Wikipedia
  • 16
    She-Devil
    35
    50

    She-Devil

    Meryl Streep, Roseanne Barr

    Released1989

    Directed bySusan Seidelman

    She-Devil is a 1989 American dark comedy film directed by Susan Seidelman and written by Barry... more on Wikipedia
  • 17
    Wuthering Heights
    29
    41

    Wuthering Heights

    Laurence Olivier, David Niven

    Released1939

    Directed byWilliam Wyler

    Wuthering Heights is a 1939 American black-and-white film directed by William Wyler and... more on Wikipedia
  • 18
    Swingers
    32
    50

    Swingers

    Heather Graham, Vince Vaughn

    Released1996

    Directed byDoug Liman

    This film is a 1996 comedy-drama film about the lives of single, unemployed actors living on... more on Wikipedia
  • 19
    After Midnight
    2
    1

    After Midnight

    Jeremy Gardner, Brea Grant

    Released2020

    Directed byJeremy Gardner

    After Midnight is a 2020 American romantic monster movie directed by Jeremy Gardner and... more on Wikipedia
  • 20
    Closer
    31
    49

    Closer

    Natalie Portman, Julia Roberts

    Released2004

    Directed byMike Nichols

    Closer is a 2004 romantic drama film written by Patrick Marber, based on his award-winning... more on Wikipedia
  • 21
    Tone-Deaf
    2
    1

    Tone-Deaf

    Amanda Crew, Robert Patrick

    Released2019

    Directed byRichard Bates Jr.

    Tone-Deaf is a 2019 American comedy horror film directed by Richard Bates Jr. After losing her... more on Wikipedia
  • 22
    Heartburn
    23
    39

    Heartburn

    Jack Nicholson, Meryl Streep

    Released1986

    Directed byMike Nichols

    Heartburn is a 1986 American comedy-drama film directed by Mike Nichols and starring Meryl... more on Wikipedia
  • 23
    The Last Five Years
    1
    1

    The Last Five Years

    Anna Kendrick, Sherie Rene Scott

    Released2014

    Directed byRichard LaGravenese

    The Last 5 Years is an upcoming American musical comedy-drama film written and directed by... more on Wikipedia
  • 24
    I'm Thinking of Ending Things
    0
    0

    I'm Thinking of Ending Things

    Jessie Buckley, Toni Collette

    Released2020

    Directed byCharlie Kaufman

    I'm Thinking of Ending Things is a 2020 American drama film directed by Charlie Kaufman, based... more on Wikipedia
  • 25
    Midnight in Paris
    7
    17

    Midnight in Paris

    Rachel McAdams, Marion Cotillard

    Released2011

    Directed byWoody Allen

    Midnight in Paris is an American 2011 romantic comedy fantasy film written and directed by... more on Wikipedia