Bottle Rocket (1996)

Ambition is a wonderful thing, as long as you've chosen the right career to be ambitious about. Wes Anderson's feature debut, "Bottle Rocket," is a quietly daffy comedy that should have been an indie hit, but was largely overlooked by audiences at the time. That's a shame, because it's a delightfully sustained caper about friends who are hopelessly unsuited to their chosen line of work. Easygoing Anthony (Luke Wilson), fresh out of a voluntary stay at a psychiatric hospital, and his high-strung pal Dignan (Owen Wilson - the two are real-life brothers) drift into a life of crime thanks to Dignan's dream of becoming a professional thief. After a few hilariously low-key practice burglaries, they recruit their friend Bob (Robert Musgrave), and soon find themselves in over their heads when they team up with seasoned criminal Mr. Henry (James Caan). Along the way, Anthony falls for Inez (Lumi Cavazos), a motel housekeeper. The humor is so relentlessly deadpan that you have to tune into its wavelength, but once you do, it fires off plenty of sparks. Owen Wilson's Dignan is a wonderfully original comic creation, so earnestly devoted to his plans that he can't see how ridiculous they are. Wilson co-wrote the screenplay with Anderson, and the film has since become a beloved cult favorite.