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The Funniest Movies About Jail 

Ranker Film
Updated April 22, 2020 764 votes 192 voters 18.4k views 24 items

List Rules Vote 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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1
Life is listed (or ranked) 1 on the list The Funniest Movies About Jail
Eddie Murphy, Poppy Montgomery, Martin Lawrence

Released: 1999

Directed by: Ted 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 ...more

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2
O Brother, Where Art Tho... is listed (or ranked) 2 on the list The Funniest Movies About Jail
George Clooney, John Goodman, Holly Hunter

Released: 2000

Directed by: Ethan 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 ...more

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3
Let's Go to Prison is listed (or ranked) 3 on the list The Funniest Movies About Jail
Will Arnett, Michael Shannon, Bob Odenkirk

Released: 2006

Directed by: Bob 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 ...more

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4
Stir Crazy is listed (or ranked) 4 on the list The Funniest Movies About Jail
Richard Pryor, Gene Wilder, Craig T. Nelson

Released: 1980

Directed by: Sidney 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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5
The Longest Yard is listed (or ranked) 5 on the list The Funniest Movies About Jail
Adam Sandler, Courteney Cox, Chris Rock

Released: 2005

Directed by: Peter 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 ...more

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6
Get Hard is listed (or ranked) 6 on the list The Funniest Movies About Jail
Alison Brie, Will Ferrell, T.I.

Released: 2015

Directed by: Etan 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 ...more
7
Chicken Run is listed (or ranked) 7 on the list The Funniest Movies About Jail
Mel Gibson, Timothy Spall, Imelda Staunton

Released: 2000

Directed by: Peter 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 ...more

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8
Holes is listed (or ranked) 8 on the list The Funniest Movies About Jail
Shia LaBeouf, Sigourney Weaver, Patricia Arquette

Released: 2003

Directed by: Andrew 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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9
Big Stan is listed (or ranked) 9 on the list The Funniest Movies About Jail
Olivia Munn, Jennifer Morrison, Rob Schneider

Released: 2007

Directed by: Rob 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 ...more
10
The Dirty Dozen is listed (or ranked) 10 on the list The Funniest Movies About Jail
Jim Brown, Donald Sutherland, Charles Bronson

Released: 1967

Directed by: Robert 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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11
Tango & Cash is listed (or ranked) 11 on the list The Funniest Movies About Jail
Sylvester Stallone, Teri Hatcher, Kurt Russell

Released: 1989

Directed by: Andrei 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 ...more

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12
Chicago is listed (or ranked) 12 on the list The Funniest Movies About Jail
Catherine Zeta-Jones, Lucy Liu, Renée Zellweger

Released: 2002

Directed by: Rob 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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13
Ernest Goes to Jail is listed (or ranked) 13 on the list The Funniest Movies About Jail
Jim Varney, Randall "Tex" Cobb, Charles Napier

Released: 1990

Directed by: John 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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14
Madea Goes to Jail is listed (or ranked) 14 on the list The Funniest Movies About Jail
Sofía Vergara, Whoopi Goldberg, Tyler Perry

Released: 2009

Directed by: Tyler 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 ...more

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15
Take the Money and Run ... is listed (or ranked) 15 on the list The Funniest Movies About Jail
Woody Allen, Louise Lasser, Lonny Chapman

Released: 1969

Directed by: Woody 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 ...more

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16
Jailhouse Rock is listed (or ranked) 16 on the list The Funniest Movies About Jail
Elvis Presley, Dean Jones, Gloria Pall

Released: 1957

Directed by: Richard 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 ...more
17
Down by Law is listed (or ranked) 17 on the list The Funniest Movies About Jail
Tom Waits, Ellen Barkin, Roberto Benigni

Released: 1986

Directed by: Jim 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, ...more

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18
I Love You Phillip Morri... is listed (or ranked) 18 on the list The Funniest Movies About Jail
Jim Carrey, Ewan McGregor, Leslie Mann

Released: 2009

Directed by: John 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. ...more

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19
Reform School Girls is listed (or ranked) 19 on the list The Funniest Movies About Jail
Wendy O. Williams, Sybil Danning, Sherri Stoner

Released: 1986

Directed by: Tom 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 ...more
20
Love is News is listed (or ranked) 20 on the list The Funniest Movies About Jail
PietraChandlerRadcliff added Tyrone Power, George Sanders, Don Ameche

Released: 1937

Directed by: Tay 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 ...more
21
Greenfingers is listed (or ranked) 21 on the list The Funniest Movies About Jail
Helen Mirren, Clive Owen, Lucy Punch

Released: 2001

Directed by: Joel 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 ...more
22
Back by Midnight is listed (or ranked) 22 on the list The Funniest Movies About Jail
Kirstie Alley, Gilbert Gottfried, Rodney Dangerfield

Released: 2005

Directed by: Harry 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 ...more
23
Mean Machine is listed (or ranked) 23 on the list The Funniest Movies About Jail
Jason Statham, Vinnie Jones, Omid Djalili

Released: 2001

Directed by: Barry 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, ...more

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24
Lucky Break is listed (or ranked) 24 on the list The Funniest Movies About Jail
Christopher Plummer, Bill Nighy, Timothy Spall

Released: 2001

Directed by: Peter Cattaneo

Lucky Break is a 2001 British comedy film starring James Nesbitt and directed by Peter Cattaneo.