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The 10 Greatest Prisoners in Film

September 19, 2012  |  7:51am

Stories revolve around conflict, and there are few settings more inherently rife with conflict, struggle and desperation than a prison. It isn’t surprising then, that Hollywood has gone to jailhouse well time and time again, either through portrayals of psychopaths trying to get out, flawed but well-intentioned ex-cons trying to stay out, the wrongfully accused trying to clear their name or defeated souls just trying to make their stay behind bars as tolerable as possible.

In honor of all the inmates of the sliver screen, we’ve compiled a list of film’s greatest prisoners. The criteria for inclusion is that the character must either have spent the majority of the film in jail, or had his time behind bars or status as an ex-convict play an integral role how he leads his life on the outside. If the character is free or on the run, we need to have been given some kind of look at what their life was like behind bars. We’re also talking about traditional, stereotypical criminal prisons (so no insane asylums or psychiatric wards), and we’re not including more than one prisoner from the same film.

Here are our top 10:

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10. Cyrus “The Virus” Grissom from Con Air
Played by John Malkovich, Cyrus The Virus takes control of a plane full of convicts and lands it in the middle of the Las Vegas strip. ‘Nough said.

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9. H.I. McDunnough from Raising Arizona
Nicolas Cage’s H.I. McDunnough seems to have resigned himself to life as an on-again-off-again jailbird until he falls in love with the prisons’ mugshot photographer, played by Holly Hunter. McDunnough is released, the two get married and he cleans up his act. When they’re unable to have a child, however, they decide to steal one from a couple that had quintuplets. Raising a child proves more cumbersome than the couple expected, especially when McDunnough’s convict friends escape from jail and expect to stay with the new family. Complications, realizations and trademark Coen Brothers hilarity ensue.

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8. Frank Morris from Escape from Alcatraz
Clint Eastwood plays bank robber Frank Morris, who is sent to Alcatraz after already having escaped from several other prisons. Morris eventually realizes that some of the concrete in his cell can be chiseled away, so he and some of the other inmates he befriends start chipping away with sharpened spoons. An escape is made, and the movie ends with Morris and company paddling away on a raft they fashioned out of raincoats.

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7. Charles Bronson from Bronson
Starring Tom Hardy as Charles Bronson (not that Charles Bronson), Bronson is based on a true story of an infamous British prisoner of the same name who has been in and (briefly) out of prison his entire life, developing a reputation for administering beatings to inmates and guards alike, taking hostages and generally stirring up a world of trouble wherever he goes. It’s hard to imagine anyone embracing life behind bars quite like Charles Bronson, who practically made a sport of it.

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6. Paul Crewe from The Longest Yard
It goes without saying that we’re talking about the original version of the film starring Burt Reynolds, not Adam Sandler’s 2005 debacle of a remake. Paul Crewe is an ex-football-player-turned-convict who fills the classic role of an inmate/protagonist who is initially despised by his fellow prisoners but ends up winning their favor. He leads a football team of inmates against the team of guards whom Crewe refused to coach. Not often are comedies set inside a jailhouse, but it works with The Longest Yard.

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5. Max Cady from Cape Fear
Robert DeNiro has proven he can go to some dark places with his characters, and few are darker, or creepier, than Max Cady. Cady is out of prison for most of the film, but the scenes of his tattooed torso and disturbing collection of books and pictures inside prison are where we truly get a sense of just how demented he’s become. Once released he relentlessly, and for the most part, legally, torments the family of Sam Bowden (Nick Nolte), who went out of his way to make sure Cady served as long of a sentence as possible.

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4. John Coffey from The Green Mile
Played by the late Michael Clarke Duncan, John Coffey is a hyper-sensitive death-row inmate and the quintessential gentle giant. The Green Mile was based on a Stephen King novel, so it shouldn’t be a huge surprise that Coffey has supernatural powers that include the ability to redistribute sicknesses and evil from one person to another. Tom Hanks plays a warden who forms a connection with Coffey, and after Coffey “shows” Hanks’ character that he’s innocent, Hanks executes him, at Coffey’s own behest.

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3. Andy Dufresne from The Shawshank Redemption
The most persistent of prisoners, Andy Dufresne takes 20 years to methodically tunnel his way out of Shawshank State Prison after he’s framed for the murder of his wife. Surrounded by fatalists, Dufresne never loses hope, and his drive eventually wins over the rest of the prisoners and even some of the guards. When he finally escapes, Red, Andy’s closest friend and the prisoner most resigned to a life behind bars, is inspired to meet Andy in Mexico after his’s granted parole.

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2. Hannibal Lecter from Silence of the Lambs
Unquestionably the most terrifying and mentally disturbed prisoner on this list is psychiatrist-turned-serial killer Hannibal Lecter. Played by Anthony Hopkins, Lecter holds the key to catching Buffalo Bill, a killer still on the loose who’s pursued by FBI agent Clarice Starling (Jodie Foster). Though kept under close surveillance, Lecter eventually escapes in horrifying fashion, but not before he’s divulged just enough information to Starling for her to discern the whereabouts of Buffalo Bill. Silence of the Lambs went on to sweep the 1991 Academy Awards, winning Oscars for Best Picture, Best Director, Best Actor, Best Actress and Best Adapted Screenplay.

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1. Luke from Cool Hand Luke
After a cop catches him cutting of the tops of parking meters, Paul Newman’s Luke is sent to prison, where his individuality and relentless anti-authoritarianism slowly earn him the respect of his fellow inmates. He becomes a Christ-like figure, continually sacrificing himself to show the other prisoners that though they are incarcerated, they are slaves to no man. (It’s no coincidence that Luke eventually meets his demise in a church after he escapes.) Though Luke is killed, what’s important is that the previously impenetrable sunglasses of the Captain are crushed as the car containing his dying body pulls away.

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