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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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Law Abiding Citizen! Would that count? He breaks out and back in?
Oh and Death Race - epic break out!
I would have to go with either The Great Escape with Steve McQueen, or Escape From Alcatraz with Clint Eastwood.
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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