The Lookout is an indie heist movie that is a better character study than it is a heist movie. Not to say that the heist is bad - if the heist wasn't there The Lookout would have been a pretty bleak and potentially dull movie.
What makes the movie is the acting. Jeff Daniels pretty much made the movie for me - trust me, he's almost worth the price of admission alone. I've only seen Joseph Gordon-Levitt in Brick (2006) and Third Rock from the Sun and now The Lookout but he's a damn fine actor. He seems well-suited for indie crime movies. The bad guys weren't anything particularly spectacular which is not a bad thing - they were just sketches of stereotypes: the manipulative leader, the Lance Henrikssen doppleganger, the musclebound get away driver, the scruffy safe cracker, and the sexpot bait.
The Lookout is definitely a winter rental, which is when it'll probably be available on DVD.
7.5 out 10.