Stupidity: Andy meets Tommy Williams who names another convict who described the scene of the murder of Andy's wife and her lover in sufficient detail to convince anyone that something was wrong with Andy's conviction. Andy then goes to the Warden, a man he knows to be utterly corrupt, a man who will suffer a huge loss if he is acquitted. Andy is an intelligent man - why would he do something as stupid as that? Why doesn't he write to his lawyer? This is a matter for an appeal court, not the Warden.
The Shawshank Redemption (1994)
1 stupidity
Directed by: Frank Darabont
Starring: Morgan Freeman, Clancy Brown, Tim Robbins, William Sadler, Bob Gunton, Gil Bellows
Factual error: When Red is sitting under the oak tree in 1967 and pulls the money out of the envelope, the top bill is signed by Nicholas F. Brady, who was Secretary of the Treasury September 1988 - January 1993. It's less about reading the handwriting as noting the different appearance of different signatures from different eras. (02:14:40)
Red: There's not a day goes by I don't feel regret. Not because I'm in here, or because you think I should. I look back on the way I was then: a young, stupid kid who committed that terrible crime. I want to talk to him. I want to try and talk some sense to him, tell him the way things are. But I can't. That kid's long gone and this old man is all that's left. I got to live with that. Rehabilitated? It's just a bullshit word. So you go on and stamp your form, sonny, and stop wasting my time. Because to tell you the truth, I don't give a shit.
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Chosen answer: In the original novella it is revealed that Andy smuggled $500 into the prison inside of his rectum. During an interview in 2004 Robbins incorrectly quoted the amount as being $100. The narration up until Red's release is provided as Red writes his account of the events while still in prison, and employs the same method to smuggle the story out. But since the issue of Andy smuggling in $500 into the prison isn't addressed in the movie, we should assume that he smuggled it in. In addition to this, the wardens scams are described as "near slave labor." From this we can assume that it is possible the inmates are getting paid (an incredibly small) wage. Perhaps Andy, with his financial knowledge, knows how to haggle, barter and stretch a dollar. One last (but not as likely) scenario is that Red allows some sort of lay by system to inmates.