Actually, I likened Leo to the Mickey Rourke film Angleheart as both films turned out to be a search for self.
In Leo you have a young, troubled boy named Leo who as part of a school assignment begins writing to Joseph Fiennes, who plays a convicted felon in prison.
When released from prison, Fiennes character sets out to meet the boy, Leo,and help both himself and Leo in the process.
Outstanding performances by Elisabeth Shue, who reprises her role as an alcholic from Leaving Las Vegas and Dennis Hopper who rules the small town's diner as Capt. Bligh ruled the HMS Bounty only with a lot more violence and sexual tension thrown in.
Sam Shepard's role serves as the Greek chorus and keeps the viewer aware of the progress of the other characters.
All in all a very good film that will captivate and entertain.