The best prison comedies

Authoritative people say that you should not despair even at those moments when fate paints a bleak picture of isolation from society for a certain number of years. After all, the same people live behind bars as in freedom, and funny stories and ridiculous cases also happen to them. We have prepared an excellent selection of films – comedies about prison.

Vacation (2018)

Nicole Stevens recently landed the coveted job of a prison guard. Trying to establish her position among experienced workers, the woman takes on a very serious and risky task – escorting the dangerous prisoner Joan to her hometown to her mother. The fact is that the mother of this “convict” is seriously ill and is about to depart for another world, and before her death she would like to see her daughter for the last time.

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36 hours of the joint journey turned out to be difficult: either the convict tried to lull Nicole’s vigilance by any tricks, or even completely escape, but all attempts were in vain. However, the main surprise awaited the escort ahead, when the dying mother suddenly began to feel great and, as it turned out, was in cahoots with her child.

Original title: 
Furlough

Starring:
Melissa Leo, Tessa Thompson, Edgar Ramirez

Country:
USA

Age limit:
16+

Be strong! (2015)

A funny American comedy about a successful investment manager James, who, by coincidence, has to spend 10 years in a maximum security colony, got into the top 10 films about prison. A rich man living in prosperity is afraid of rumors that he will not be able to survive without becoming someone’s “bitch” in the zone.

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Having managed to win a month’s reprieve from the court, James decided to take prisoner courses. To this end, he has hired Darmell, a car washer, to train his boss on how not to perish behind bars. Having turned the mansion into a prison, a black cellmate for 30 days comes up with a whole series of stupid tests, mocking his boss to his heart’s content.

Original Title:
Get Hard

Cast:
Will Ferrell, Kevin Hart, Craig T. Nelson

Country:
USA

Age Limit:
18+

Cellmates (2011)

Leroy Lowe is a fierce racist who ended up behind bars for inciting conflicts. But sometimes fate is very cruel and presents very unexpected surprises – his cellmate turned out to be the Hispanic Emilio, that is, the one whom Lowe hates so vehemently.

Left without the support of the same fanatics as he is, Leroy is infuriated only at the thought that he is forced to share a cell with a “Latino”. Every day, inventing and implementing various dirty tricks for his neighbor and trying to turn his life into hell, the spiteful critic is amazed at Emilio’s stamina. However, this is not the worst thing that the hero of this funny film will face.

Original title:
Cellmates

Starring:
Tom Sizemore, Stacy Keach, Kevin P. Farley

Country:
USA

Age limit:
16+

Madea in Jail (2009)

A great comedy about a crazy American granny whose behavior eventually landed her in jail. The whole district knew an old woman named Madea: she is rude and foul, cheats and fights, a train of adventures “on the verge of a foul” constantly trails behind her.

In the end, the grandmother was once again caught, and the judge gladly gave her a sentence of edification. However, it soon became clear that Madea was not at all afraid of prison and felt at home there like a fish in water. She quickly settled down and began to restore her order in the colony.

Original title:
Madea Goes to Jail

Starring:
Tyler Perry, Derek Luke, Keshia Knight Pulliam

Country:
USA

Age limit:
12+

Big Stan (2007)

Stan Minton is a successful realtor and a scammer at the same time. Once he sold an old woman a cabin in a Negro ghetto, telling the customer that the object of sale was a beautiful villa with friendly neighbors. This time the number did not pass, and Minton fell under investigation.

Having “greased” the judge and paid off all the savings with him, Stan managed to agree and get a term not “to the fullest”, but only a few years. Immediately before being sent to the zone, the hero takes a series of lessons from a martial arts master – a local bum. Now the hero of the film considers himself able to protect himself from sexual harassment in the zone.

Original title:
Big Stan

Cast:
Rob Schneider, David Carradine, Jennifer Morrison

Country:
USA

Age limit:
16+

All or Nothing (2005)

An excellent comedy about a US prison, the order prevailing in it and how the hero copes with them. Paul Crewe once successfully played for the National Football Team, and after graduating from his sports career, he was caught driving while drunk. American laws in this part are harsh, and the former athlete had to go to jail.

The head of the colony decided to organize a match between the guards and the convicts, in which Paul was destined for a special role. He had to do everything to make the prisoners lose. For this, Crewe was promised an early release.

Original title: 
The Longest Yard

Cast:
Adam Sandler, Chris Rock, Burt Reynolds

Country:
USA

Age limit:
16+

Prison Activists (2003)

In our age of emancipation, it is no secret to anyone that a woman is capable of many things, especially being in extreme conditions. This hilarious comedy upends the conventional wisdom about hard, almost unbearable life in most modern colonies.

The main character, nicknamed Jackpot, drinks refreshing cocktails in the cell and “rules” the sucker-guards with might and main, extracting the necessary information from them. Another strange character in the film is a questionable scientist who performs suspicious experiments on female prisoners. In this unusual prison colony, under the leadership of Jackpot, a female militant group of activists is formed.

Título original:
Prison-A-Go-Go!

Cast:
Rhonda Shire, Mary Voronov, Laurie Walton

Country:
USA

Age limit:
16+

Bonebreaker (2001)

Continuing our list of comedies about prison is a funny film about not going limp and hoping for the best even when things go awry. Danny Meehan leads the English football team. He is rich, famous, surrounded by the love of the public and the attention of women.

One day, this happy life ends at once – Danny “on a drunken bench” attacks a police officer and receives for this no less than a three-year term in a colony. The only one who was delighted with such a turn in the fate of the famous athlete was the head of the prison. After all, under his command is his own team, which will now be coached by the legendary football player. Meehan doesn’t mind becoming the coach, but asks the “boss” to let the guard team play against the cons under Danny.

Original title:
Mean Machine

Starring:
Vinnie Jones, Jason Statham, Jason Fleming

Country:
UK, USA

Age limit:
16+

Gift of Destiny (2001)

Rudy and James decided to do something extraordinary that would allow them to enter the category of “elite” criminals once and for all. To do this, the guys decided not to waste money on trifles, but immediately start with a big fish – rob a bank .

Due to the fact that the plan was a little unfinished, and frankly, mediocre, the guys were captured, and they went to work on the mistakes for 12 years in the Long Radford prison. Once behind bars, Rudy and James immediately began to think over an escape plan. Their participation in a stupid musical composed by the head of the colony could help in the implementation of the plan. Now, in order to escape from the hated prison, the heroes will have to show their dancing and vocal skills.

Original title:
Lucky Break

Starring:
James Nesbitt, Olivia Williams, Timothy Spall

Country:
UK, Germany

Age limit:
16+

For life (1999)

Our selection of films is completed by a comedy about two idiots who foolishly ended up in one of the US prisons. Banks was an ordinary bank worker, and Gibson was a petty thief. The men managed to anger the local mafia boss, and he gave them a task that they could not refuse on pain of death.

The mission was “uncomplicated”, given that the action takes place during Prohibition. The guys had to smuggle a truck full of smuggled alcohol across half the country. Naturally, the unfortunate workers failed, were caught by the police and sentenced to life. Now Banks and Gibson will spend the rest of their lives behind bars if they don’t figure out how to escape.

Original title:
Life

Cast:
Eddie Murphy, Martin Lawrence, Obba Babatunde

Country:
USA 

Age limit:
16+

Do you know other funny movies about prison? Add to the list of comedies in the comments!

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Jared Lambert/ author of the article

I’ve been writing about movies, TV shows and anime for over 3 years, and you may have seen my reviews on Rotten Tomatoes and Metacritic.

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