The Funniest Movies About Jail

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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Ranked by
  • Stir Crazy
    1
    Gene Wilder, Richard Pryor, Georg Stanford Brown
    • Released: 1980
    • Directed by: Sidney Poitier
  • O Brother, Where Art Thou?
    2
    George Clooney, John Turturro, Tim Blake Nelson
    • Released: 2000
    • Directed by: Joel Coen
  • Life
    3
    Eddie Murphy, Martin Lawrence, Obba Babatunde
    • Released: 1999
    • Directed by: Ted Demme
  • Let's Go to Prison
    4
    Dax Shepard, Will Arnett, Chi McBride
    • Released: 2006
    • Directed by: Bob Odenkirk
  • Chicken Run
    5
    Mel Gibson, Julia Sawalha, Miranda Richardson
    • Released: 2000
    • Directed by: Peter Lord, Nick Park
  • Big Stan
    6
    Olivia Munn, Jennifer Morrison, Rob Schneider
    • Released: 2007
    • Directed by: Rob Schneider
  • The Longest Yard
    7
    Adam Sandler, Chris Rock, Burt Reynolds
    • Released: 2005
    • Directed by: Peter Segal
  • Get Hard
    8
    Will Ferrell, Kevin Hart, Craig T. Nelson
    • Released: 2015
    • Directed by: Etan Cohen
  • Holes
    9
    Sigourney Weaver, Jon Voight, Patricia Arquette
    • Released: 2003
    • Directed by: Andrew Davis
  • Tango & Cash
    10
    Sylvester Stallone, Kurt Russell, Teri Hatcher
    • Released: 1989
    • Directed by: Andrey Konchalovskiy
  • Ernest Goes to Jail
    11
    Jim Varney, Gailard Sartain, Bill Byrge
    • Released: 1990
    • Directed by: John R. Cherry
  • The Dirty Dozen
    12
    Lee Marvin, Ernest Borgnine, Charles Bronson
    • Released: 1967
    • Directed by: Robert Aldrich
  • Chicago
    13
    Catherine Zeta-Jones, Renée Zellweger, Richard Gere
    • Released: 2002
    • Directed by: Rob Marshall
  • Down by Law
    14
    Tom Waits, Ellen Barkin, Roberto Benigni
    • Released: 1986
    • Directed by: Jim Jarmusch
  • Madea Goes to Jail
    15
    Tyler Perry, Derek Luke, Keshia Knight Pulliam
    • Released: 2009
    • Directed by: Tyler Perry
  • Take the Money and Run
    16
    Woody Allen, Janet Margolin, Marcel Hillaire
    • Released: 1969
    • Directed by: Woody Allen
  • Jailhouse Rock
    17
    Elvis Presley, Judy Tyler, Mickey Shaughnessy
    • Released: 1957
    • Directed by: Richard Thorpe
  • I Love You Phillip Morris
    18
    Jim Carrey, Ewan McGregor, Leslie Mann
    • Released: 2009
    • Directed by: Glenn Ficarra, John Requa
  • Love is News
    19
    Tyrone Power, Loretta Young, Don Ameche
    • Released: 1937
    • Directed by: Tay Garnett

    great jail scene!

  • Greenfingers
    20
    Clive Owen, Helen Mirren, David Kelly
    • Released: 2000
    • Directed by: Joel Hershman
  • Reform School Girls
    21
    Wendy O. Williams, Sybil Danning, Sherri Stoner
    • Released: 1986
    • Directed by: Tom DeSimone
  • Mean Machine
    22
    Jason Statham, Vinnie Jones, Omid Djalili
    • Released: 2001
    • Directed by: Barry Skolnick
  • Lucky Break
    23
    Gia Carides, Anthony LaPaglia, Rebecca Gibney
    • Released: 1994
    • Directed by: Ben Lewin
  • Back by Midnight
    24
    Kirstie Alley, Gilbert Gottfried, Rodney Dangerfield
    • Released: 2005
    • Directed by: Harry Basil