The Truman Show
This movie seems to get more and more relevant each time I see it, what with people spending more and more of their lives in virtual worlds, and scenarios like the Matrix seemingly a real possibility, as gaming technology accelerates. (Cough, Wii.) But anyway, it's a really smart story, very well done, and a great combination of comedy and some pretty powerful drama. And believe it or not, Jim Carey is pretty good in it. Go watch it now!