Run Ronnie Run is the essence of underrated. The movie is based on the character of Ronnie Dobbs from Mr. Show with Bob and Dave. The movie got held up by the production company, went straight to DVD, and was disowned by the creators due to their disgust with the final edit. Most fans of the show hate it and Bob has a rant about it on thier website where recommends renting it if you choose to watch it because he thinks the final version is such a turd. I don't think a movie could come with any less fanfare. As for the movie itself, it is the story of a redneck being recruited to do a Cops-esque reality show where he gets arrested every week. Chock full of hillarious scenes. David Koechner is especially funny as Ronnie's drunken sidekick Clay.
Shakes the Clown, written and directed by Bobcat Goldthwait is the story of an alcoholic clown. How could that not be raved by critics? Actually, a very funny social commentary about in groups and out groups. Watch for Robin Williams as a mime instructor.
A Cool Dry Place, Vince Vaughn plays a single father struggling to find a way to balance his career and taking care of his son after his wife bolts. Total chick flick, but very heartwarming. Rent this one for date night and your wife/girlfriend will be pleased.
The Fisher King, the other Holy Grail film directed by Terry Gilliam. In typical Gilliam fashion this modern day parable skirts between fantasy and reality. Jeff Bridges plays a Stern-esque radio shock jock whose comments send a listner over the edge resulting in him losing his career and falling into depression. He seeks redemption by befriending a mentally-ill homeless man played by Robin Williams on his quest to find the Holy Grail.
Dead Presidents, this Hughes Bros effort tackles the issue of the involvment of African Americans in the Viet Nam War. Very interesting combination of social commentary and war dramatization mixed into a heist film. The war scenes are not for the faint of heart.
A Galaxy Far, Far Away, I almost forgot this one. The only reason I even know about it is because I know the director. Documentary following the Star Wars phenomenon shot during the time leading up to the release of Episode I. Made with zero budget but still very funny. Unless you have Netflix or something similar, you'll have to buy this one. Not going to find it at the local video store.