Bottle Rocket (1996) was the first film directed by Wes Anderson. He co-wrote the screenplay with Owen Wilson, who plays one of the main characters, Dignan. Not as ornate and baroque as Anderson's later films, this one is nonetheless characteristically a Wes Anderson film. It's wacky, chaotic, random, and whimsical. The two main characters, Dignan and Anthony (Luke Wilson), both of whom have just been released from a mental hospital, are neurotically paranoid and dysfunctional. They aspire to be robbers. The Wilson brothers, especially Chris Wilson, are so flaky and spaced that they enhance the random quality of what happens. Dignan plans out their heists in obsessive detail, with maps and secret codes and events timed to the second. Their first robbery is at a bookstore.
Although there was a screenplay, the film feels as if it were entirely improvised. I can't really say that there's a plot: this is a film about crazy characters and cracked aspirations. In the climactic scene, with the assistance of accomplices (including an Indian safecracker who seems on the verge of senility) Dignan and Anthony try to rob a warehouse. Carefully planned though this heist might be, it devolves into an anarchistic and hilarious mess. Everything goes wrong.
At times the film seems to wander off course, but such wanderings are characteristic of Wes Anderson's films. They're not wanderings at all. An example occurs at a motel where Dignan and Anthony have holed up after their bookstore robbery. Anthony falls passionately in love with a young housekeeper. He follows her from one room to the other, helps her clean and make the beds. They swim together and finally make love in one of the rooms. She's from Paraguay, he doesn't speak Spanish, so they can’t communicate. You never know what's going to happen next. Another bit of randomness is the appearance of James Caan as Mr. Henry, who heads up a small-time crime ring masquerading as a landscape service. Caan fits right in.
Anderson uses in Bottle Rocket a number of actors who appear in his later films, especially the Wilson brothers. One example is Kumar Pallana, the safecracker: he played secondary characters in Rushmore (1998), The Royal Tenenbaums (2001), and The Darjeeling Limited (2007).