Best Prison Comedy Films to Watch

Best Prison Comedy Films to Watch Comedies about Unusual Places

There's something uniquely amusing about the juxtaposition of the grim setting of a prison with the light-hearted antics of comedy. This collection of films showcases the lighter side of incarceration, where inmates find humor in their dire situations, plan the most ridiculous escapes, and form unlikely friendships. From classic slapstick to clever satires, these films offer a comedic escape from the daily grind, proving that laughter can indeed be found behind bars.

The Jerk (1979)
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The Jerk (1979)

Description: While not entirely set in prison, Steve Martin's character does spend time in jail, and his naive reactions to incarceration provide some of the film's funniest moments.

Fact: Steve Martin wrote the screenplay, which was his first major film role.

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Stir Crazy (1980)
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Stir Crazy (1980)

Description: Two friends, played by Gene Wilder and Richard Pryor, are wrongfully convicted and sent to prison. Their attempts to adapt to prison life and their eventual escape plan provide plenty of laughs.

Fact: The film was one of the highest-grossing comedies of its time, showcasing the comedic chemistry between Wilder and Pryor.

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Down by Law (1986)
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Down by Law (1986)

Description: Directed by Jim Jarmusch, this film follows three men who end up in the same cell. Their interactions and eventual escape attempt are filled with dry humor and existential musings.

Fact: The film features Tom Waits and John Lurie, both known for their contributions to music as well as acting.

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The Shawshank Redemption (1994)
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The Shawshank Redemption (1994)

Description: While not strictly a comedy, this film's blend of drama and humor, particularly through the character of Red, makes it a fitting inclusion. It's about hope, friendship, and the occasional chuckle amidst the bleakness of prison life.

Fact: The film was not a box office hit initially but has since become one of the most beloved films, often topping IMDb's top 250 list.

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The Longest Yard (2005)
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The Longest Yard (2005)

Description: Adam Sandler stars in this remake of the 1974 film, where a disgraced former NFL quarterback organizes a football game between inmates and guards. The humor comes from the absurdity of the situation and the characters' antics.

Fact: The film features a mix of real NFL players and actors, adding to the authenticity of the football scenes.

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Get Hard (2015)
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Get Hard (2015)

Description: Will Ferrell's character hires Kevin Hart to prepare him for prison life, leading to a series of comedic training sessions and misunderstandings about what prison life entails.

Fact: The film was criticized for its portrayal of racial stereotypes but was praised for the comedic performances of Ferrell and Hart.

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Life (1999)
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Life (1999)

Description: Eddie Murphy and Martin Lawrence star as two friends wrongfully convicted of murder, serving life sentences. Their misadventures and comedic attempts to survive prison life make this film a standout in the genre.

Fact: The film was shot in a real prison, Angola State Penitentiary in Louisiana, which added to the authenticity of the setting.

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Let's Go to Prison (2006)
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Let's Go to Prison (2006)

Description: A man, seeking revenge for his father's wrongful imprisonment, gets himself arrested to torment the son of the judge who sentenced his father. The film is filled with slapstick humor and absurd situations.

Fact: The film was directed by Bob Odenkirk, better known for his work in comedy writing and acting.

This movie is not available on Amazon Prime, but you can use the bonus:
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Big Stan (2007)
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Big Stan (2007)

Description: Rob Schneider plays a real estate con artist who learns martial arts to survive in prison. The film is filled with Schneider's brand of humor, focusing on his character's transformation.

Fact: The film was directed by Rob Schneider himself, showcasing his versatility in the industry.

This movie is not available on Amazon Prime, but you can use the bonus:
Amazon Prime Video 30 Days Free
The Escapist (2008)
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The Escapist (2008)

Description: While primarily a thriller, this film has moments of dark humor as a group of inmates plan an elaborate escape. The tension and the cleverness of the plan provide comedic relief.

Fact: The film was shot in real prison locations in Ireland, giving it a gritty, authentic feel.

This movie is not available on Amazon Prime, but you can use the bonus:
Amazon Prime Video 30 Days Free
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