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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)
2
O Brother, Where Art Thou? (2000)
O Brother, Where Art Thou? (2000)
3
Stir Crazy (1980)
Stir Crazy (1980)
4
Chicken Run (2000)
Chicken Run (2000)
5
Holes (2003)
Holes (2003)
6
Cry-Baby (1990)
Cry-Baby (1990)
7
Down by Law (1986)
Down by Law (1986)
8
Tango & Cash (1989)
Tango & Cash (1989)
9
I Love You Phillip Morris (2009)
I Love You Phillip Morris (2009)
10
Get Hard (2015)
Get Hard (2015)
11
The Hoose-Gow (1929)
The Hoose-Gow (1929)
12
Harold & Kumar Escape From Guantanamo Bay (2008)
Harold & Kumar Escape From Guantanamo Bay (2008)
13
Life (1999)
Life (1999)
14
Take the Money and Run (1969)
Take the Money and Run (1969)
15
Ernest Goes to Jail (1990)
Ernest Goes to Jail (1990)
16
Chopper (2000)
Chopper (2000)
17
Madea Goes to Jail (2009)
Madea Goes to Jail (2009)
18
Let's Go to Prison (2006)
Let's Go to Prison (2006)
19
Mean Machine (2001)
Mean Machine (2001)
20
Big Stan (2007)
Big Stan (2007)
21
Convict 13 (1920)
Convict 13 (1920)
22
Reform School Girls (1986)
Reform School Girls (1986)
23
Greenfingers (2001)
Greenfingers (2001)
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)
32
Go for Broke (2002)
Go for Broke (2002)
33
Jail Birds of Paradise (1934)
Jail Birds of Paradise (1934)
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