The Shawshank Redemption (1994) - Tops on any list.
The Blues Brothers (1980) - Of course they'll never get caught. They're on a mission from Gyod! Also features one of the best soundtracks in film. Don't bother with any of the sequels however.
Papillon (1973) - Steve McQueen and Dustin Hoffman at their best. "Hey you bastards, I'm still here".
Cool Hand Luke (1967) - Stars Paul Newman, but the star of the show is George Kennedy with his Oscar winning performance as best supporting actor.
The Longest Yard (1965 - TV) - The 1974 version starring Burt Reynolds, not the 2005 version starring Adam Sandler.
Escape From Alcatraz (1979) - Clint Eastwood plays Frank Morris, the only man believed to have escaped from the rock. Morris's method was even proven possible on Mythbusters.
American History X (1998) - Powerful film that tackles racism and hatred head on.
Bad Boys (1983) - The version with Sean Penn not the one with Martin Lawrence and Will Smith.
The Birdman of Alcatraz (1962) - John Frankenheimer direction that features Burt Lancaster as Robert Stroud, a prisoner who was probably the most famous inmate ever to reside on Alcatraz.
The Deer Hunter (1978) - Robert DeNiro and Christopher Walken in the 5-time Academy Award winner. Though not a prison movie per se, it certainly features on the most oppressive and intense POW scenes in film.
O Brother Where Art Thou (2000) - Coen brothers interpretation of The Odyssey that stars George Clooney, John Turturro, and John Goodman. Also a great soundtrack worth owning.
Bridge on the River Kwai (1957) - One of the best war movies of all time as well.
Midnight Express (1978) - Note to self: never try to smuggle hash out of Turkey.
The Great Escape (1963) - Steve McQueen makes the list again in this 1963 epic that featured an ensemble cast of near heroes.
The Green Mile (1999) - A Stephen King product that featured the breakout performance of Michael Clarke Duncan.
Dead Man Walking (1995) - Say what you will about Sean Penn, but he's good in this one!
Chicago (2002) - Yes, it's a prison movie.
48 Hours (1982) - Prison movies can be funny too.
Chicken Run (2000) - Well, not prison as we know it, but it is chicken prison nonetheless.
Stalag 17 (1960) - A Billy Wilder film with William Holden as a prisoner in a WWII German POW camp. Inspired the hit television series, Hogan's Heroes (1965)
The Hurricane (1999) - Another gripping performance by Denzel Washington as Rubin "Hurricane" Carter, a boxer wrongly imprisoned for murder
My Cousin Vinny (1992) - In case you need more proof that prison movies can be funny. Stars Joe Pesci and Marisa Tomei.
Stir Crazy (1980) - One of Richard Pryor's funniest movies. Who would have imagined the chemistry between Pryor and Gene Wilder? Directed by Sydney Poitier.
Alien 3 (1992) - Sigourney Weaver's space pod crashes on a remote prison planet. Let the mayhem begin.
The Life of David Gale (2003) - One of the most controversial films on the list. Stars Kevin Spacey and Kate Winslet.
25th Hour (2002) - A Spike Lee joint. What goes on in a man's life as he spends his final day before doing a seven year prison term.
21 Grams (2003) - While questionable as to whether or not it qualifies as a prison movie, it does feature Sean Penn and Naomi Watts in one of the best performances by Naomi Watts' nipples.
Paradise Lost: The Child Murders at Robin Hood Hills (1996) - No fiction writer would dare make an attempt at presenting such an unbelievable story of inept police work and plot implausibility.
The Great Raid (2005) - John Daul film based on the William B. Breuer book of one of the bravest acts in military history that no one knows about.
Brubaker (1980) - Starring Robert Redford as the titular warden, this film won a Best Original Screenplay Oscar for its writer, W.D. Richter. Yes, it's that good.
Blood in, Blood Out (1993) - Based on the true life experiences of poet Jimmy Santiago Baca and other members of an East L.A. gang, the film depicts how a violent crime and the influence of narcotics alter their lives. So as not to promote gang violence, Disney actually released the film under the banner "Bound By Honor" since "Blood In, Blood Out" is the motto of La Onda, the prison gang depicted in the film.
The McKenzie Break (1970) - In the closing days of World War II, German prisoners riot in a POW Camp in Scotland. Fearful of a mass escape attempt, the British Army sends in an unorthodox Irish Captain (in the person of Brian Keith) in hopes of discovering exactly what is going on. A true multinational production - the setting is Scotland, the film was made largely on location in Ireland with a cast of British, American and German actors, produced and directed by Americans."
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