Kimberly O'Brien Chicago: Top 25 Divorce and Breakup Movies
by kimberlyobrienchicago | created - 13 Jun 2014 | updated - 13 Jun 2014 | PublicThe best movies about divorces and/or breakups!
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1. Le divorce (2003)
PG-13 | 117 min | Comedy, Drama, Romance
French vs. American social customs and behaviors are observed in a story about an American visiting her sister and French brother-in-law and niece in Paris.
Director: James Ivory | Stars: Kate Hudson, Naomi Watts, Stockard Channing, Jean-Marie Lhomme
Votes: 12,081 | Gross: $9.07M
2. Under the Tuscan Sun (2003)
PG-13 | 113 min | Comedy, Drama, Romance
Frances Mayes, a 35-year-old San Francisco writer, gets a divorce that leaves her with terminal writer's block and depression. Later, she decides to buy a house in Tuscany in order to change her life.
Director: Audrey Wells | Stars: Diane Lane, Raoul Bova, Sandra Oh, Lindsay Duncan
Votes: 59,513 | Gross: $43.61M
3. Sideways (2004)
R | 127 min | Comedy, Drama, Romance
Two men reaching middle age with not much to show but disappointment embark on a week-long road trip through California's wine country, just as one is about to take a trip down the aisle.
Director: Alexander Payne | Stars: Paul Giamatti, Thomas Haden Church, Virginia Madsen, Sandra Oh
Votes: 204,202 | Gross: $71.50M
4. Annie Hall (1977)
PG | 93 min | Comedy, Romance
Alvy Singer, a divorced Jewish comedian, reflects on his relationship with ex-lover Annie Hall, an aspiring nightclub singer, which ended abruptly just like his previous marriages.
Director: Woody Allen | Stars: Woody Allen, Diane Keaton, Tony Roberts, Carol Kane
Votes: 278,323 | Gross: $39.20M
5. Kramer vs. Kramer (1979)
PG | 105 min | Drama
After his wife leaves him, a work-obsessed Manhattan advertising executive is forced to learn long-neglected parenting skills, but a heated custody battle over the couple's young son deepens the wounds left by the separation.
Director: Robert Benton | Stars: Dustin Hoffman, Meryl Streep, Jane Alexander, Justin Henry
Votes: 154,649 | Gross: $106.26M
6. Eternal Sunshine of the Spotless Mind (2004)
R | 108 min | Drama, Romance, Sci-Fi
When their relationship turns sour, a couple undergoes a medical procedure to have each other erased from their memories forever.
Director: Michel Gondry | Stars: Jim Carrey, Kate Winslet, Tom Wilkinson, Gerry Robert Byrne
Votes: 1,077,624 | Gross: $34.40M
7. Chicago (2002)
PG-13 | 113 min | Comedy, Crime, Musical
Two death-row murderesses develop a fierce rivalry while competing for publicity, celebrity, and a sleazy lawyer's attention.
Director: Rob Marshall | Stars: Renée Zellweger, Catherine Zeta-Jones, Richard Gere, Taye Diggs
Votes: 243,307 | Gross: $170.69M
8. The Accidental Tourist (1988)
PG | 121 min | Comedy, Drama, Romance
An emotionally distant writer of travel guides must carry on with his life after his son is killed and his marriage crumbles.
Director: Lawrence Kasdan | Stars: William Hurt, Kathleen Turner, Geena Davis, Amy Wright
Votes: 17,273 | Gross: $32.63M
9. High Fidelity (2000)
R | 113 min | Comedy, Drama, Music
Rob, a record store owner and compulsive list maker, recounts his top five breakups, including the one in progress.
Director: Stephen Frears | Stars: John Cusack, Iben Hjejle, Todd Louiso, Jack Black
Votes: 189,724 | Gross: $27.29M
10. The War of the Roses (1989)
R | 116 min | Comedy, Romance
A married couple tries everything to drive each other out of the house in a vicious divorce battle.
Director: Danny DeVito | Stars: Michael Douglas, Kathleen Turner, Danny DeVito, Marianne Sägebrecht
Votes: 57,354 | Gross: $86.89M
11. Blue Valentine (2010)
R | 112 min | Drama, Romance
The relationship of a contemporary married couple, charting their evolution over a span of years by cross-cutting between time periods.
Director: Derek Cianfrance | Stars: Ryan Gosling, Michelle Williams, John Doman, Faith Wladyka
Votes: 211,296 | Gross: $9.74M
12. The Squid and the Whale (2005)
R | 81 min | Comedy, Drama
Follows two young boys dealing with their parents' divorce in Brooklyn in the 1980s.
Director: Noah Baumbach | Stars: Owen Kline, Jeff Daniels, Laura Linney, Jesse Eisenberg
Votes: 90,412 | Gross: $7.36M
13. Mrs. Doubtfire (1993)
PG-13 | 125 min | Comedy, Drama
After a bitter divorce, an actor disguises himself as a female housekeeper to spend time with his children held in custody by his former wife.
Director: Chris Columbus | Stars: Robin Williams, Sally Field, Pierce Brosnan, Harvey Fierstein
Votes: 290,827 | Gross: $219.20M
14. The Parent Trap (1961)
Passed | 129 min | Comedy, Family, Romance
Teenage twin sisters swap places and scheme to reunite their divorced parents.
Director: David Swift | Stars: Hayley Mills, Maureen O'Hara, Brian Keith, Charles Ruggles
Votes: 23,963
15. Mr. Wonderful (1993)
PG-13 | 98 min | Comedy, Romance
In an attempt to end alimony payments, a working class man tries to set up his ex wife with potential husbands.
Director: Anthony Minghella | Stars: Matt Dillon, Annabella Sciorra, Mary-Louise Parker, William Hurt
Votes: 3,537 | Gross: $3.13M
16. Waiting to Exhale (1995)
R | 124 min | Comedy, Drama, Romance
Based on Terry McMillan's novel, this film follows four very different African-American women and their relationships with men.
Director: Forest Whitaker | Stars: Whitney Houston, Angela Bassett, Loretta Devine, Lela Rochon
Votes: 12,190 | Gross: $67.05M
17. Liar Liar (1997)
PG-13 | 86 min | Comedy, Fantasy
A pathological liar-lawyer finds his career turned upside down when he inexplicably cannot physically lie for 24 whole hours.
Director: Tom Shadyac | Stars: Jim Carrey, Maura Tierney, Amanda Donohoe, Jennifer Tilly
Votes: 333,284 | Gross: $181.41M
18. Along Came Polly (2004)
PG-13 | 90 min | Comedy, Romance
A buttoned-up newlywed finds his strictly organized life descend into chaos when he falls in love with an old classmate.
Director: John Hamburg | Stars: Ben Stiller, Jennifer Aniston, Debra Messing, Philip Seymour Hoffman
Votes: 143,632 | Gross: $88.10M
19. The Way We Were (1973)
PG | 118 min | Drama, Romance
During post-WWII McCarthyism, a diametrically opposed couple come together only to find out that genuine friendship and physical attraction is not enough to overcome fundamental societal beliefs.
Director: Sydney Pollack | Stars: Barbra Streisand, Robert Redford, Bradford Dillman, Lois Chiles
Votes: 27,465
20. The Break-Up (2006)
PG-13 | 106 min | Comedy, Drama, Romance
A couple's break-up proceeds to get uglier and nastier by the moment as each tries to keep their luxurious condo from the other.
Director: Peyton Reed | Stars: Jennifer Aniston, Vince Vaughn, Jon Favreau, Joey Lauren Adams
Votes: 138,954 | Gross: $118.70M
21. The Royal Tenenbaums (2001)
R | 110 min | Comedy, Drama
The eccentric members of a dysfunctional family reluctantly gather under the same roof for various reasons.
Director: Wes Anderson | Stars: Gene Hackman, Gwyneth Paltrow, Anjelica Huston, Ben Stiller
Votes: 313,087 | Gross: $52.36M
22. Broken Flowers (2005)
R | 106 min | Comedy, Drama, Mystery
As the extremely withdrawn Don Johnston is dumped by his latest woman, he receives an anonymous letter from a former lover informing him that he has a son who may be looking for him. A freelance sleuth neighbor moves Don to embark on a cross-country search for his old flames in search of answers.
Director: Jim Jarmusch | Stars: Bill Murray, Jessica Lange, Sharon Stone, Julie Delpy
Votes: 106,796 | Gross: $13.74M
23. Parenthood (1989)
PG-13 | 124 min | Comedy, Drama
Four Buckman siblings attempt to raise their children - each in their own different style - and deal with the joys and sorrows that the process brings.
Director: Ron Howard | Stars: Steve Martin, Mary Steenburgen, Dianne Wiest, Jason Robards
Votes: 54,855 | Gross: $100.05M
24. Leaving Las Vegas (1995)
R | 111 min | Drama, Romance
Ben Sanderson, a Hollywood screenwriter who lost everything because of his alcoholism, arrives in Las Vegas to drink himself to death. There, he meets and forms an uneasy friendship and non-interference pact with prostitute Sera.
Director: Mike Figgis | Stars: Nicolas Cage, Elisabeth Shue, Julian Sands, Richard Lewis
Votes: 134,608 | Gross: $32.03M
25. Old School (2003)
R | 88 min | Comedy
Three friends attempt to recapture their glory days by opening up a fraternity near their alma mater.
Director: Todd Phillips | Stars: Luke Wilson, Vince Vaughn, Will Ferrell, Jeremy Piven
Votes: 243,293 | Gross: $75.59M
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