The Princess Bride (1987)

What, you've never seen this movie? Inconceivable! Christopher Guest plays the villainous Count Rugen, who works in a hollow tree, just like the Keebler Elves. Oh, except he tortures people instead of making cookies. Mmmm, cookies.

The Big Picture (1989)

Guest directed this movie about a young director (Kevin Bacon) selling his soul to Hollywood. I assume it's autobiographical. Michael McKean plays the best friend. Funny and a little surreal.

Party Girl (1995)

Parker Posey plays a frivolous New Yorker who discovers the joys of the Dewey decimal system. No, it's fun, really.

Ghost World (2001)

Bob Balaban plays the loving but ineffectual father to a cynical teen in this movie that I absolutely loved.

Breaking Away (1979)

Speaking of loving but ineffectual fathers, Paul Dooley played one here. He's frustrated because his son likes to ride bikes and pretend to be Italian. And really, who can blame him? Bikes are dangerous.