The Shawshank Redemption
Mr. Smith Goes to Washington
Pirates of Silicon Valley
11–20 of 151 posts
The Shawshank Redemption
Mr. Smith Goes to Washington
Pirates of Silicon Valley
The Bourne Identity.
From IMDB: In an afterlife resembling the present-day US, people must prove their worth by showing in court how they have demonstrated courage.
Albert Brooks dies and has to prove that he has conquered his fears in order to "move on" or get smarter.
He looks back on his life and sees how things could have been better if he'd just had more courage.
I'll answer my own question: Catch Me If You Can (2002). It's basically the adventures of a very skilled social engineer.