The Wendell Baker Story (2005)
Written by Luke Wilson, who also stars, and directed by Luke and his brother Andrew Wilson, this was surprisingly charming and funny. It's about a laid-back, not yet financially successful con-man who's stringing his girlfriend along until he can make some real money. But then he gets caught and goes to prison, where he seems to be having such a good time that his girlfriend dumps him for good. Regret and reformation ensue as he tries to win her back after he's paroled. Besides Luke Wilson, you get Eva Mendes as Doreen the girlfriend, Owen Wilson as the slimy operator of a "retirement hotel," Will Ferrell as Doreen's new boyfriend with a real job (manager of a grocery store), and several other entertaining and well-acted side characters. I really liked it.