I love the theme in these movies. The Red character towards the end, and the Lester character, are too scared/or something personal holding them back, to live life the way they want to live it. Can anyone think of any other movies, with similar themes? I asked this question over on the IMDB, but everyone keeps naming off prison movies. I'm looking for movies, where the main character, is eat up with fear, or something personal holding them back, to do the things, they really, really want to do. And of course, they eventually get to do those things, in the movie.

Joe Versus the Volcanoe

In current theatrical release: LITTLE CHILDREN.

A couple of Leo DiCaprio films:
What's Eating Gilbert Grape
This Boy's Life

Good Will Hunting

The Truman Show

I'll have to watch Truman again. I haven't seen it, in a few years. I've only seen bits of WEGG, I'll watch it all soon. And Good WIll Hunting is a good choice. I forgot about that one.

I will get to that one.

Honeymoon in Vegas

What About Bob?

Fight Club

At first I thought you were just talking about Thomas Newman scores.

The Boy Who could Fly

Some good suggestions so far. I especially like Joe versus the Volcano.

Another one that hasn't been mentioned that might fit, Office Space.