The 10 Greatest Movie Prisoners of All-Time

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In what I would consider to be one of the few movies that I’ll always leave on without exception, Shawshank was on television last night.  And I’m not talking TNT Television.  It was on cable so there were no commercials and no aggravation.  Just a fantastic movie.  Easily in my top three.  And then I got to thinking.  I used to watch Oz as well.  Prison is just such great drama isn’t it?  So I thought about writing a list of the best TV prisoners. Unfortunately when I was done it contained 4 guys from Oz, 5 guys from Prison Break and George Bluth Sr. from Arrested Development.

So rather than screw that up, here are what I consider to be the 10 best prisoners from movies.

10) Il Duce (The Boondock Saints)

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A relatively minor character compared to some on this list, the Boondock boy’s father was feared nationwide, and required nothing short of a small army to transport him place to place. But once he realized he was on the wrong side of things, quickly turned from a terrifying enemy to an invaluable asset.

9) Cyrus the Virus (Con Air)

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There was a whole plane full of prisoners to choose from here, but ultimately I decided on the film’s main villain Cyrus the Virus. Sure, Steven Buscemi was an excellent loony serial killer, and Nic Cage was well, Nic Cage (oh that hair!), but only Cyrus had the brains the brawn to orchestrate an elaborate mid-air prison bolt, and for that he deserves a spot on the list.

8 ) John Patrick Mason (The Rock)

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The only man to ever escape from Alcatraz is enlisted by the government to something something something BOOM! BAM! EXPLODING HELICOPTERS! FERRARIS! Sean Connery may have not have been in tip top form as the escapee, but he was certainly the shining point of the Michael Bay-helmed explosion fest The Rock.

7) Derek Vinyard (American History X)

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Usually we think of Nazis as the scum of the earth, but Derek Vinyard went from skinhead to upstanding citizen after his stay in jail for the murder (curbstomping!) of a black man. Sure the rape may have helped in his conversion, but however he got there, it’s one of the most profound prison reforms seen on film.

6) Andy Dufresne (The Shawshank Redemption)

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Probably the most normal out of any of the guys on this list, Andy Dufresne was a man wrongly accused, and for years he suffered in relative silence. But what no one else knew was that he had begun an excavation project, and after years of wrongful imprisonment, finally tunneled his way to salvation. Plus he had to hang out with that Morgan Freeman all day, and you know that HAS to be a huge pain.

5) John Coffey (The Green Mile)

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Another Steven King-written prisoner, Coffey and Dufresne were both wrongly accused, but the similarities stopped there. The titan of a man was somehow gifted with healing powers, which Tom Hank’s testes found completely delightful and refreshing. No he didn’t escape, but he left an impact well after he was gone nonetheless.

4) Edmond Dantes (The Count of Monte Cristo)

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I don’t think that anyone else on this list had worse living conditions than Edmund Dantes. You’ve seen “The Hole” in prison movies and shows before. A dark empty room made of stone with no interaction with others. It was for prisoners who had misbehaved. Well, because this was ye olden days, ALL prison cells were the hole, and Edmund had been framed by his best friend for treason so he could marry his girlfriend. That, my friends, is an awful hand in the game of life. But he took that hand and after escaping made his life a polar opposite what it was, finally getting ultimate revenge on the man who caused it all.

3) Luke (Cool Hand Luke)

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Famous for escaping and egg-eating, Luke is one cool cat. Sure his spirit gets broken by some truly nasty guards, but it doesn’t matter, his heart shines through in the end. Luke was one of Paul Newman’s greatest roles, and helped to earn him a secure place as a film icon.

2) Hannibal Lecter (The Silence of the Lambs)

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I’d say Hannibal takes the cake for being the flat out most dangerous prisoner on the list. Yes, he will eat your liver for dinner, but he’s also a master of mind games and will use his surprisingly large amount of charm to get you just where he wants you. And then he’ll eat your liver with some Fava beans for dinner.

1) Capt. Hilts “The Cooler King” (The Great Escape)

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The only prisoner on this list to be inspired by a true story, Capt. Hilts helped 76 men escape from an SS-run POW camp during World War II. If that wasn’t enough, he himself tries to escape by jumping a motorcycle over a barbed wired fence. Sure he doesn’t make it, but plenty of style points awarded for trying.

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