Bottle Rocket

A 1996 film starring Owen Wilson, Luke Wilson, and James Caan, and directed by Wes Anderson. This film marked the major acting debut of both Owen and Luke Wilson and was Wes Anderon's directing debut.

After Anthony Adams (Luke) is released from a mental hospital following a nervous breakdown, his longtime friend Dignan (Owen) convinces him to join him and their mutual friend Robert (Robert Musgrave) on a crime spree to prove themselves to the "legendary" Mr. Henry. It quickly becomes apparent that these three are in over their heads and have no idea what they are doing. Hilarity Ensues.

The film ultimately only screened in 48 theaters and never managed to recover its $7 million dollar budget.

This film contains examples of these tropes:

 * Adaptation Expansion: The film is based on a short film made by Wes Anderson and starring Owen and Luke Wilson, also called "Bottle Rocket." It's basically the part where Dignan and Anthony steal from Anthony's house.
 * Badass Grandpa: Mr. Henry, who stands up to and overpowers the younger and larger Future Man.
 * Bittersweet Ending:
 * The Caper: Dignan is committed to getting into heists as part of his life plan. Anthony goes along with it because he has nothing better to do.
 * Chekhov's Gun: While "trying out" as a getaway driver with Dignan, Bob tells him he's risk taker, since he's growing an entire crop of marijuana in his parent's backyard. Later, Bob discovers his brother, Future Man, is in prison because the police discovered the weed and believed he was a drug dealer.
 * Everyone Calls Him "Barkeep": Bob's brother is only ever referred to as Future Man by the main characters, though he introduces himself as "John Maplethorpe."
 * Real Life Relative: Future Man is played by Owen and Luke's older brother Andrew.
 * Shout Out:
 * Dignan introduces himself and Bob to Inez in the hotel room as Jerry and Cornelius. Jerry Cornelius is a character from Michael Moorcock's books such as "The Cure for Cancer" and "The Final Program".
 * Dignan and Anthony steal an Alfa Romeo Spider, the car from The Graduate, another film about youthful ennui.