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I would say the answer is probably 'The Defiant Ones' starring Sidney Poitier and Tony Curtis (1958). That movie set the template for all others films of the sub-genre that followed it, I think.
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I would have to go with either The Great Escape with Steve McQueen, or Escape From Alcatraz with Clint Eastwood.
Law Abiding Citizen! Would that count? He breaks out and back in?
Oh and Death Race - epic break out!
My choice would definitely be - The Shawshank Redemption.
I just saw it on the old movie chanel over the weekend ...The Great Escape!
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