14 American Prison Comedy Movies

Some do not understand foreign humor, considering it silly and superficial. However, there are pictures that everyone will like, if not jokes, then certainly the plot: American comedies about prison. Fascinating stories and funny play of the main characters will not let boredom even those who tiredly collapsed on the couch after a hard day’s work.


  • IMDB Rating – 5.5
  • Genre: Drama, Comedy
  • Production: USA / 2018
  • US box office receipts: $8,472
  • Director: Lori Collier
  • Starring: Melissa Leo, Tessa Thompson, Edgar Ramirez, Eric Griffin, Drena De Niro, La La Anthony, Damien Lemon, Suzanne Shepherd, Michael Chernus, Dolly Wells

The plot unfolds in a correctional institution, one of the few where not only men but also women hold responsible positions. Trainee Nicole is given the opportunity to show what she can do, and for the first time in the history of the prison, they trust a girl to transport a prisoner.

Despite her current sentence, she is allowed to go home for a few days to visit her terminally ill mother. These 36 hours will be a real nightmare for Nicole, and in the end it turns out that her mother’s illness is just an excuse.

The film had its first screening in 2018 at Sundance, a major independent film festival.

14 American Prison Comedy Movies

Henry’s Crime

Henry's Crime
  • IMDB Rating – 6.0
  • Genre: Melodrama, comedy, crime
  • Production: USA / 2011
  • Budget: $12,000,000
  • Worldwide Box Office: $204,940
  • Director: Malcolm Venville
  • Starring: Keanu Reeves, James Caan, Vera Farmiga, Peter Stormare, Judy Greer, Danny Hoch, Fisher Stevens, Curry Graham, David Costabile, Bill Duke.

The list of American comedies about prison would simply not be complete if we did not include this movie, which has become in a sense a classic. At the same time, it differs significantly from the others, first of all, with an intricate script.

Dull fellow Henry lives in his Godforsaken booth, surviving on small tolls from passers-by. And all would be nothing, but one day he meets a guy who asks him to wait at the entrance to the bank.

What’s the big deal, you ask? Henry ends up waiting not for his buddy, but for three years in prison on a robbery charge. But his time will come too, because any term has a way of ending….

The bank featured in the film is a real financial institution in Buffalo, opened back in 1901.

14 American Prison Comedy Movies

Get Hard

Get Hard!
  • IMDB Rating – 6.0
  • Genre: Comedy, Crime
  • Production: USA / 2015
  • Budget: $40,000,000
  • Worldwide Box Office: $111,711,453
  • Director: Ethan Coen
  • Starring: Will Ferrell, Kevin Hart, Craig T. Nelson, Alison Brie, Edwina Findlay, Ariana Neal, Eric Chavarria, T.I., Paul Ben-Victor, John Mayer

An office plankton learns that he has been framed, and of course, he is about to serve his sentence in a correctional facility. Fearing that he will not be accepted by his cellmates due to his lack of experience and ignorance of prison ethics, he enlists the help of his hired hand – a window washer, a black inmate.

And by golly, it’s really funny! What the protagonist, a former “white collar” man, performed, listening to his former “mentor” in everything, deserves special attention.

This is the first feature film directed by Ethan Coen. In case you don’t know, this man created “Men in Black” and “Madagascar 2”.

From the funny part: the episode of falling off the yacht is a real filming failure. After the characters swim in the water, they climb back up completely dry.

14 American Prison Comedy Movies

Let’s Go to Prison

Let's Go to Prison
  • IMDB Rating – 6.0
  • Genre: Comedy, Crime
  • Production: USA / 2006
  • US box office receipts: $4,630,045
  • Director: Bob Odenkirk
  • Starring: Dex Shepard, Will Arnett, Chi McBride, David Cockner, Dylan Baker, Michael Shannon, Miguel Nino, Jay Whitaker, Amy Hill, David Darlow

If you do not like American comedies and do not perceive movies about prison, then this picture will definitely change your opinion. This is frankly black humor, which will be to the taste of gourmets only.

Perfect in timing the movie (only 86 minutes) is filled with very funny and fascinating episodes, during which the main character John Lisicki takes false accusations and goes to prison. Except that this story doesn’t end so easily for the judge…..

The director and screenwriter did an incredible thing: a comedy, designed to entertain only, they turned it into a good thriller (if I may say so), which keeps in suspense until the end and makes the viewer follow the behavior of the characters very carefully, because it is in them that the main answer is hidden.

One of the scenes can rightfully be considered a reference to the famous movie “Taxi Driver”: the main character appears several times in the same clothes.

14 American Prison Comedy Movies


  • IMDB Rating – 5.6
  • Genre: Drama, comedy
  • Production: USA / 2011
  • Budget: $2,000,000
  • Director: Jesse Baje
  • Starring: Tom Sizemore, Stacy Keach, Kevin P. Farley, Hector Jimenez, Olga Segura, Bob Rickard, Rock Williams, Tom Gulager, Kai Sturdivant, Leighton R. Shields.

A good comedy drama is rare because, as a rule, filmmakers get either the former or the latter. We will not claim that this movie was an exception, but we will give you this opportunity.

An activist of one clan, an ordinary worker from Mexico and a principled racist find themselves in the same cell… Sounds like the beginning of a joke, right? But it’s not.

The fights don’t stop there, it literally comes down to the allocation of boundaries drawn in chalk on the floor and walls, and the irony is that the most important thing, the toilet, is only on one of the allocated sectors.

And yes, these guys will eventually become friends. But what is the reason for such a unity and reconciliation of three completely different, and even hating each other initially, people?

This movie, by the way, is also about the power of love.

The debut of director Jesse Baje, after watching which critics were divided exactly in two – some loved it, others hated it. Apparently, they decided to adopt the behavior of the characters.

14 American Prison Comedy Movies

I Love You Phillip Morris

I Love You Phillip Morris
  • IMDB Rating – 6.6
  • Genre: Drama, Melodrama, Comedy, Crime, Biography
  • Production: France, USA / 2008
  • Budget: $13,000,000
  • Worldwide box office receipts: $20,768,906
  • Director: Glenn Ficarra, John Recua
  • Starring: Jim Carrey, Ewan McGregor, Leslie Mann, Rodrigo Santoro, Anthony Corone, Brennan Brown, Michael Mandell, Annie Golden, Marylouise Burke, David Jensen.

And in this movie you will be able to look at your favorite Jim Carrey in a different way: he has never had such a funny, but at the same time sensual, frank and sensitive role before.

The story is very ambiguous for the Russian viewer: an exemplary adult family man, loving husband and father, goes to prison, where he falls in love with another prisoner.

But that’s not even the point. The point is that this is one of the few pictures that did not disgust any man who came to the screening in the distant 2008. We are talking about men from Russia, where attitudes towards gays are still more negative than neutral.

One hardened heterosexual resident of Siberia, if we are to believe the review, admitted that after watching the movie he even liked blond Philip.

In domestic distribution the role of Jim Carrey was entrusted to voice Timur Batrutdinov (and not for the first time), and Ewan – Peter Fedorov.

The movie wanted to ban in the United States because of her “excessive homosexuality”. Fortunately, it was not banned.

14 American Prison Comedy Movies

Madea Goes to Jail

Madea Goes to Jail
  • IMDB Rating – 4.5
  • Genre: Drama, Comedy, Crime
  • Production: USA / 2009
  • US box office receipts: $90,508,336
  • Director: Tyler Perry
  • Starring: Tyler Perry, Derek Luke, Keshia Knight Pulliam, David Mann, Tamela J. Mann, RonRico Lee, Ion Overman, Vanessa Ferlito, Viola Davis, Sofia Vergara.

A woman named Madea goes to prison for consequences committed in fits of anger. And we all know what happens to the unruly in penitentiaries…. But the prisoner even there manages not to be discouraged, time after time getting into ridiculous and funny situations, thereby putting the wardens in a total stupor.

They love her, and hate her, and punish her, and help her…. In general, a classic melodrama, and in this case this characterization is exclusively positive.

The slogan fits perfectly to what is happening on the screen: “Something big is coming to your house”.

The authors note that it is better to avoid watching the movie for those under 14 years of age.

14 American Prison Comedy Movies

Big Stan

Big Stan
  • IMDB Rating – 6.2
  • Genre: Action, comedy
  • Production: USA / 2007
  • Budget: $10,000,000
  • Worldwide Box Office: $7,926,235
  • Director: Rob Schneider
  • Starring: Rob Schneider, David Carradine, Jennifer Morrison, Scott Wilson, Henry Gibson, M. Emmet Walsh, Sally Kirkland, Jackson Rathbone, Bob Sapp, Richard Kaind.

Stan lives a quiet and prosperous life, dealing in dubious but lucrative affairs: cheating gullible old ladies, forcing them to buy a house in openly criminal neighborhoods. Being carried away by machinations, the hero makes a mistake and he is sentenced, but thanks to money and connections he manages to get a 5-month reprieve.

Having met the prison “guru”, Stan begins to undergo intensive preparation for prison: he tattoos his anus, expands it with a big dildo and practices everything that, according to the stories of others, awaits him in the future. Of course, his wife leaves him and disappears in search of a better life, or at least not so crazy.

The frail and puny guy, after the appointed months, meets the prisoners, and thanks to his experience, changes absolutely all the orders, turning the once terrible colony into an institution for pacifists. But this, to put it mildly, does not quite suit the warden, who has his own plans, which are just the opposite.

The directorial debut of Rob Schneider, who also starred in the movie.

It also stars Pilar Schneider, his mother.

14 American Prison Comedy Movies

Find Me Guilty

Find Me Guilty
  • IMDB Rating – 7.0
  • Genre: Drama, comedy, crime, biography
  • Production: USA, Germany / 2006
  • Budget: $13,000,000
  • Worldwide Box Office: $2,636,637
  • Director: Sidney Lumet
  • Starring: Vin Diesel, Peter Dinklage, Lynas Roach, Ron Silver, Annabella Sciorra, Alex Rocco, Frank Pietrangolare, Richard DeDomenico, Jerry Grayson, Tony Ray Rossi.

This legal tragicomedy is the penultimate brainchild of Sidney Lumet. The main roles were taken by handsome Vin Diesel and charismatic Peter Dinklage.

The movie is based on real events. And it is a real drama about the trial of the Lucchese mafia clan, which became the longest in the history of the United States.

The prisoner Jackie returns to the dock, there he is waiting for his associates, for whom he unexpectedly refuses a lawyer, taking his own defense on himself.

The tape was never released in Russian distribution.

This is the best film about thieves’ honor according to American critics.

14 American Prison Comedy Movies

The Longest Yard

The Longest Yard
  • IMDB Rating – 6.4
  • Genre: Crime, Sports, Comedy
  • Production: USA / 2005
  • Budget: $82,000,000
  • Worldwide Box Office: $190,320,568
  • Director: Peter Segal
  • Starring: Adam Sandler, Chris Rock, Burt Reynolds, James Cromwell, William Fichtner, Nelly, Michael Irvin, Bob Sapp, Nicholas Turturro, Terry Crews.

Successful soccer player Paul Crewe sometimes gets a little too much out of control, but he always gets away with it. But not this time: he is caught and convicted of drunk driving.

The prison governor, treating the prisoner with the utmost respect and nobility, offers the guys to organize a soccer match, and, of course, the recruitment of one of the teams entrusted to Paul. There is one “but”: the main person of the penitentiary loves himself more, so he offers the captain of the team to reduce the term in case the guards win.

Don’t think that you guess about the ending of this story: everything is quite different.

Steve Austin, while preparing for filming, got so involved in training that he tore a tendon under his knee.

Filming tape was held in a closed institution, the walls of which have undergone the largest in the history of America riots. The case was February 2, 1980. Read it if you’re interested – it’s never been done again.

14 American Prison Comedy Movies


  • IMDB Rating – 3.9
  • Genre: Action, comedy
  • Production: USA / 2003
  • Director: Barak Epstein
  • Starring: Rhonda Scheer, Mary Crow, Lori Walton, Travis Willingham, Lauren Graham, Luisa Lawless, Tina Parker, Ilram Choi, Mike Wiebe, May Moreno.

Imagine 12 people of completely different ages, races, religions, and just plain outlooks on life in one room. And if they are also emotional women, the explosion is unavoidable.

This is exactly what happens in the comedy film by Barak Epstein, who so ironically and satirically presented this story that the audience can only sit in front of the screen and be in shock from the understanding of what the weaker sex is capable of.

The picture is prohibited for children and teenagers under the age of 18.

14 American Prison Comedy Movies

Mean Machine

Mean Machine
  • IMDB Rating – 6.5
  • Genre: Drama, Comedy, Crime, Sports
  • Production: UK, USA / 2001
  • Budget: £2,500,000
  • Worldwide Box Office: $7,310,206
  • Director: Barry Skolnick
  • Starring: Vinnie Jones, Jason Statham, Jason Fleming, David E. Kelley, David Hemmings, Ralph Brown, Wes Blackwood, Robbie Gee, Joff Bell, John Forgem.

Another comedy classic, this time from Barry Skolnick, and another story about a soccer player whose permissiveness has opened the gates of a penal institution for him.

He is a successful and rich soccer player, captain of the English national team, and a terrible debauchee. However, payback for mischief, though late, but still caught up with Danny Meehan – three years in prison for assaulting an officer. Money and connections didn’t help, as law enforcement officers are overly reverent in this country.

But even in prison soccer does not leave him: having organized his own team, he offers the wardens to fight with prisoners, and they do not mind – no one believes in the victory of beaten criminals.

The project is a remake of the coolest movie of 1974 “The Longest Yard”.

Vinnie Jones, before becoming an actor, was a professional soccer player, and not an ordinary one either: he played for the famous Chelsea club, where he got the nickname “Bonesaw”.

14 American Prison Comedy Movies

Lucky Break

Lucky Break
  • IMDB Rating – 6.2
  • Genre: Melodrama, Comedy, Crime
  • Production: UK, Germany, USA / 2001
  • Budget: $6,000,000
  • US box office receipts: $54,606
  • Director: Peter Cattaneo
  • Starring: James Nesbitt, Olivia Williams, Timothy Spall, Bill Nye, Lennie James, Ron Cook, Frank Harper, Raymond Waring, Christopher Plummer, Julian Barrett.

The coolest film with James Nesbitt, at the sight of which you already want to smile, and if he also plays in a comedy movie, it forever becomes unforgettable.

The picture begins very strangely: once violent criminals of the prison “Long Radford”, characterized by a lack of culture and any moral principles, suddenly, unexpectedly for all, change into ancient costumes and wigs, begin to engage in dancing and singing …

And after a short time, they already play brilliantly in the play, but what is strange – a terrible and untalented play … Maybe they’re up to something?

Stephen Fry’s script will definitely catch you off guard.

The box office revenue amounted to over 2,500,000 million dollars.

The film was created by representatives of three countries at once: England, Germany and America.

14 American Prison Comedy Movies


  • IMDB Rating – 6.8
  • Genre: Drama, Comedy, Crime
  • Production: USA / 1999
  • Budget: $80,000,000
  • Worldwide Box Office: $73,345,029
  • Director: Ted Demme
  • Starring: Eddie Murphy, Martin Lawrence, Obba Babatunde, Nick Cassavetes, Anthony Anderson, Barry Shebaka Henley, Brent Jennings, Bernie Mac, Miguel A. Nunez, Jr.

The fact that the main role was played by Eddie Murphy, already makes you watch and personally appreciate the picture. By the way, his consistently terrific performance is complemented by the talent of director Ted Demme, who has long since carved out a niche for himself in American cinema.

Willie Long is an old inmate who has been in a Mississippi correctional facility for many years, where a very non-comedic event takes place. The thing is that in the infirmary there is a fire, as a result of which two of his best friends die. He was allowed to attend the funeral, but he did not keep quiet and decided to tell the two guys digging graves, the story of the dead. And here’s the really interesting part.

Rick Baker won the Academy Award for Best Makeup in 2000.

The song most often heard in the movie became an American hit for several years. It is about R Kelly’s track “Fortunate”.

14 American Prison Comedy Movies
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Анна Румянцева
Anna Rumyantseva

Author, editor and filmmaker.

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