If you've never seen American Movie, you are really missing out.  It's a documentary about Mark Borchardt, a guy from the Milwaukee area trying to make a horror movie.  What makes American Movie amazing is not necessarily Borchardt and his quest, but the crazy "cast" of characters around him.  His friends and family are a riot to watch and it's hard to believe that they are not actors and it's not scripted.

American Movie may be hard to find in your local stores, but is easily available at many of the larger online retailers if you're interested.