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The Funniest Jailhouse Comedy Films

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. How many of these films have you seen???
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How many have you seen???

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1
Chicago (2002)
Chicago (2002)
Rotten Tomatoes®   86%
2
O Brother, Where Art Thou? (2000)
O Brother, Where Art Thou? (2000)
Rotten Tomatoes®   78%
3
Stir Crazy (1980)
Stir Crazy (1980)
Rotten Tomatoes®   67%
4
Chicken Run (2000)
Chicken Run (2000)
Rotten Tomatoes®   97%
5
Holes (2003)
Holes (2003)
Rotten Tomatoes®   78%
6
Cry-Baby (1990)
Cry-Baby (1990)
Rotten Tomatoes®   73%
7
Down by Law (1986)
Down by Law (1986)
Rotten Tomatoes®   87%
8
Tango & Cash (1989)
Tango & Cash (1989)
Rotten Tomatoes®   30%
9
I Love You Phillip Morris (2009)
I Love You Phillip Morris (2009)
Rotten Tomatoes®   71%
10
Get Hard (2015)
Get Hard (2015)
Rotten Tomatoes®   28%
11
The Hoose-Gow (1929)
The Hoose-Gow (1929)
12
Harold & Kumar Escape From Guantanamo Bay (2008)
Harold & Kumar Escape From Guantanamo Bay (2008)
Rotten Tomatoes®   52%
13
Life (1999)
Life (1999)
Rotten Tomatoes®   51%
14
Take the Money and Run (1969)
Take the Money and Run (1969)
Rotten Tomatoes®   91%
15
Ernest Goes to Jail (1990)
Ernest Goes to Jail (1990)
Rotten Tomatoes®   11%
16
Chopper (2000)
Chopper (2000)
Rotten Tomatoes®   74%
17
Madea Goes to Jail (2009)
Madea Goes to Jail (2009)
Rotten Tomatoes®   29%
18
Let's Go to Prison (2006)
Let's Go to Prison (2006)
Rotten Tomatoes®   13%
19
Mean Machine (2001)
Mean Machine (2001)
Rotten Tomatoes®   34%
20
Big Stan (2007)
Big Stan (2007)
Rotten Tomatoes®   11%
21
Convict 13 (1920)
Convict 13 (1920)
22
Reform School Girls (1986)
Reform School Girls (1986)
Rotten Tomatoes®   25%
23
Greenfingers (2001)
Greenfingers (2001)
Rotten Tomatoes®   46%
24
Pardon Us (1931)
Pardon Us (1931)
25
Love Is News (1937)
Love Is News (1937)
26
Back by Midnight (2005)
Back by Midnight (2005)
27
Big House Bunny (1950)
Big House Bunny (1950)
28
Doin' Time (1985)
Doin' Time (1985)
29
Hold 'em Jail (1932)
Hold 'em Jail (1932)
30
Pros & Cons (1999)
Pros & Cons (1999)
31
Paperback Romance (1994)
Paperback Romance (1994)
Rotten Tomatoes®   33%
32
Go for Broke (2002)
Go for Broke (2002)
33
Jail Birds of Paradise (1934)
Jail Birds of Paradise (1934)
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