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240 voters

The Funniest Movies About Jail

Updated April 22, 2020 1.2k votes 240 voters 26.2k views24 items

List RulesVote up the most hilarious comedies about life in jail for prisoners.

Some of the best prison movies are so funny it's almost criminal. The top funny movies about jail feature hilarious actors trying to escape prison, or making the most of their life behind bars. This is a list of the greatest comedies about jail including everything from The Longest Yard to Jailhouse Rock to Take the Money and Run.

What films will you find on this list of prison comedy movies? Chicago puts a musical spin on the criminal life, following a pair of murderous women as they attempt to stay in the news. Stir Crazy is another hilarious movie about prison. With Eddie Murphy and Martin Lawrence in the lead roles, it should come as no surprise that Life was one of the funniest movies of 1999. Other good movies featured on this list include Let's Go to Prison, Lucky Break, and Big Stan.

It's up to you to decide which prison comedy deserves the top spot on this list. Give your favorites a thumbs up to move them to number one, and please add any good movies that are missing.

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    Let's Go to Prison

    Will Arnett, Michael Shannon

    Released2006

    Directed byBob Odenkirk

    Let's Go to Prison is an American comedy that was released in theatres November 17, 2006, starring Dax Shepard, Will Arnett and Chi McBride, and directed by Bob Odenkirk. The movie was loosely based...  more

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    54
    22

    O Brother, Where Art Thou?

    George Clooney, John Goodman

    Released2000

    Directed byEthan Coen, Joel Coen

    O Brother, Where Art Thou? is a 2000 adventure comedy film written, produced, edited, and directed by Joel and Ethan Coen, and starring George Clooney, John Turturro, and Tim Blake Nelson, with John...  more

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    47
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    Stir Crazy

    Richard Pryor, Gene Wilder

    Released1980

    Directed bySidney Poitier

    Stir Crazy is a 1980 American comedy film directed by Sidney Poitier and starring Gene Wilder and Richard Pryor as down-on-their-luck friends who are given 125-year prison sentences after being...  more

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  • 4
    51
    26

    Life

    Eddie Murphy, Poppy Montgomery

    Released1999

    Directed byTed Demme

    Life is a 1999 American comedy-drama film written by Robert Ramsey & Matthew Stone and directed by Ted Demme. The film stars Eddie Murphy and Martin Lawrence. The supporting cast includes Obba...  more

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    The Longest Yard

    Adam Sandler, Courteney Cox

    Released2005

    Directed byPeter Segal

    The Longest Yard is a 2005 American sports comedy film, a remake of the 1974 film of the same name. Adam Sandler plays the protagonist, Paul Crewe, a disgraced former professional quarterback for the...  more

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    37
    15

    Madea Goes to Jail

    Sofía Vergara, Whoopi Goldberg

    Released2009

    Directed byTyler Perry

    Madea Goes to Jail is a 2009 parodic comedy-drama film written and directed by Tyler Perry, which was based on his 2006 play. The play and the film deal with Perry's recurring character Madea going...  more

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  • 7
    34
    15

    Chicken Run

    Mel Gibson, Timothy Spall

    Released2000

    Directed byPeter Lord, Nick Park

    Chicken Run is a 2000 British-French-American stop-motion animated comedy film made by the Aardman Animations studios and directed by Peter Lord and Nick Park. Chicken Run received positive reviews,...  more

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  • 8
    38
    19

    Get Hard

    Alison Brie, Will Ferrell

    Released2015

    Directed byEtan Cohen

    Get Hard is an American comedy film directed by Etan Cohen and written by Etan Cohen, Jay Martel and Ian Roberts. The film stars Will Ferrell, Kevin Hart, Alison Brie, Edwina Findley, and Craig T....  more
  • 9
    48
    34

    Chicago

    Catherine Zeta-Jones, Lucy Liu

    Released2002

    Directed byRob Marshall

    Chicago is a 2002 American musical comedy film adapted from the satirical stage musical of the same name, exploring the themes of celebrity, scandal, and corruption in Jazz Age Chicago. The film...  more

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  • 10
    26
    11

    Holes

    Shia LaBeouf, Sigourney Weaver

    Released2003

    Directed byAndrew Davis

    Holes is a 2003 American comedy-drama adventure film based on the 1998 novel of the same title by Louis Sachar, with Shia LaBeouf as the lead role of Stanley Yelnats IV and also starring Khleo...  more

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    Ernest Goes to Jail

    Jim Varney, Randall "Tex" Cobb

    Released1990

    Directed byJohn R. Cherry III

    Ernest Goes to Jail is a 1990 comedy film directed by John R. Cherry III and starring Jim Varney. It is the fourth film to feature the character Ernest P. Worrell. It was shot in Nashville and...  more
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    35
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    Big Stan

    Olivia Munn, Jennifer Morrison

    Released2007

    Directed byRob Schneider

    Big Stan is a 2007 American comedy film directed and produced by Rob Schneider, who also starred in the film. The film co-stars Jennifer Morrison, Scott Wilson and David Carradine. Although released...  more
  • 13
    9
    12

    Reform School Girls

    Wendy O. Williams, Sybil Danning

    Released1986

    Directed byTom DeSimone

    Reform School Girls is a 1986 American film, written and directed by Tom DeSimone. It stars Linda Carol, Wendy O. Williams, Pat Ast, Sybil Danning and Sherri Stoner, and depicts the story of Jenny, a...  more
  • 14
    19
    27

    Tango & Cash

    Sylvester Stallone, Teri Hatcher

    Released1989

    Directed byAndrei Konchalovsky, Albert Magnoli

    Tango & Cash is a 1989 American buddy cop action comedy film directed by Andrei Konchalovsky, although Albert Magnoli took over in the later stages of filming, and starring Sylvester Stallone, Kurt...  more

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  • 15
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    35

    Jailhouse Rock

    Elvis Presley, Dean Jones

    Released1957

    Directed byRichard Thorpe

    Jailhouse Rock is a 1957 American musical drama film directed by Richard Thorpe and starring Elvis Presley, Judy Tyler, and Mickey Shaughnessy. Distributed by Metro-Goldwyn-Mayer and dramatized by...  more
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    22
    33

    The Dirty Dozen

    Jim Brown, Donald Sutherland

    Released1967

    Directed byRobert Aldrich

    The Dirty Dozen is a 1967 film directed by Robert Aldrich, released by MGM, and starring Lee Marvin. The picture was filmed in England and features an ensemble supporting cast including Ernest...  more

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  • 17
    9
    14

    Back by Midnight

    Kirstie Alley, Gilbert Gottfried

    Released2005

    Directed byHarry Basil

    Back By Midnight is a 2005 comedy film starring Rodney Dangerfield, Phil LaMarr, Harland Williams, Randy Quaid, Gilbert Gottfried, and Kirstie Alley. The film was completed in 2002. It also features...  more
  • 18
    20
    33

    I Love You Phillip Morris

    Jim Carrey, Ewan McGregor

    Released2009

    Directed byJohn Requa, Glenn Ficarra

    I Love You Phillip Morris is a 2009 comedy film based on the 1980s and '90s real-life story of con artist, impostor, and multiple prison escapee Steven Jay Russell, as played by Jim Carrey. While...  more

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  • 19
    8
    16

    Lucky Break

    Christopher Plummer, Bill Nighy

    Released2001

    Directed byPeter Cattaneo

    Lucky Break is a 2001 British comedy film starring James Nesbitt and directed by Peter Cattaneo....  more
  • 20
    5
    15

    Love is News

    Tyrone Power, George Sanders

    Released1937

    Directed byTay Garnett

    great jail scene!

    Love Is News is a 1937 romantic film starring Tyrone Power, Loretta Young, and Don Ameche. The movie was directed by Tay Garnett and was the first film for which Power had top billing. The picture...  more
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    10
    25

    Down by Law

    Tom Waits, Ellen Barkin

    Released1986

    Directed byJim Jarmusch

    Down by Law is a 1986 black-and-white independent film written and directed by Jim Jarmusch. It stars Tom Waits, John Lurie, and Roberto Benigni. The film centers on the arrest, incarceration, and...  more

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  • 22
    16
    35

    Take the Money and Run

    Woody Allen, Louise Lasser

    Released1969

    Directed byWoody Allen

    Take the Money and Run is a 1969 American comedic mockumentary directed by Woody Allen and starring Allen and Janet Margolin. Written by Allen and Mickey Rose, the film chronicles the life of Virgil...  more

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  • 23
    12
    43

    Mean Machine

    Jason Statham, Vinnie Jones

    Released2001

    Directed byBarry Skolnick

    Mean Machine is a 2001 British comedy-drama film directed by Barry Skolnick. It stars former footballer Vinnie Jones. The film is an adaptation of the 1974 American film The Longest Yard, featuring...  more
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    7
    23

    Greenfingers

    Helen Mirren, Clive Owen

    Released2001

    Directed byJoel Hershman

    Greenfingers is a 2000 British comedy film directed and written by Joel Hershman. It is loosely based on a true story about the award-winning prisoners of HMP Leyhill, a minimum-security prison in...  more