Plot
In Texas, Dignan (Owen C. Wilson) "rescues" Anthony (Luke Wilson) from a voluntary mental hospital, where he has been staying for self-described exhaustion. Dignan has an elaborate escape planned and has developed a 75-year plan that he shows to Anthony. The plan is to pull off several heists and then meet Mr. Henry, a landscaper and part-time criminal known to Dignan.
As a practice heist, the two friends break into Anthony's house, stealing specific items from a list. Afterward, critiquing the heist, Dignan reveals that he took a pair of earrings, not specified on the list. This upsets Anthony, as he had bought those earrings for his mother. Anthony visits his little sister at her school so she can return the earrings. Dignan recruits Bob Mapplethorpe (Robert Musgrave) as a getaway driver because he is the only person they know with a car. The three buy guns and return to Bob's house to plan their next heist, a local bookstore. The group bickers as Dignan struggles to describe his intricate plan.
The group steals a small sum of money from the bookstore and "go on the lam" at a hotel. Anthony meets Inés (Lumi Cavazos), a maid, and the two spark a romance despite Inés's lack of English. Bob learns that his marijuana crop has been discovered by police and his older brother has been arrested. Bob leaves to help his brother. Before leaving, Anthony gives Dignan an envelope for Inés. Dignan delivers the envelope to Inés while she is cleaning a room, not knowing the envelope has most of his and Anthony's money inside. Inés does not open the envelope and hugs Dignan to say goodbye. As Dignan is leaving, Inés asks an English-speaking male friend of hers to chase after Dignan and tell him she loves Anthony. When he delivers the message he says, "Tell Anthony I love him". Dignan fails to realize he is speaking for Inés and does not deliver the message.
Taking an abandoned Alfa Romeo Spider, Dignan and Anthony continue with the 75-year plan, but the car breaks down. Anthony reveals that the envelope Dignan gave to Inés contained the rest of their cash. The two get in a fight and go their separate ways. Narrating a letter to his sister, Anthony says he and Bob have settled into a routine that is keeping them busy. Dignan, who has joined Mr. Henry's gang, tracks Anthony down and they reconcile. Dignan invites Anthony into a job with Mr. Henry and Anthony accepts on the condition that Bob is allowed in. The trio meet the eccentric Mr. Henry (James Caan) and plan to rob a safe at a cold storage facility. Mr. Henry becomes a role model for the trio, standing up to Bob's abusive brother and tutoring Dignan on success. He invites the trio to a party at his house and visits the group at the Mapplethorpes' house, which he compliments. Anthony learns of Inés's love for him and contacts her. She has learned some English and the two rekindle their relationship.
With two accomplices from Mr. Henry's landscaping company, the group conducts their heist at the factory, but the plan quickly falls apart. As the police arrive, Dignan has locked himself out of the escape van and is arrested. During the heist, Mr. Henry loads furniture from Bob's house into a truck. Anthony and Bob visit Dignan in prison and tell him how Mr. Henry robbed Bob's house. Dignan begins rattling off an escape plan and tells his friends to get into position for a get-away. After a tense moment the two realize Dignan is joking. Dignan says to Anthony, "Isn't it funny that you used to be in the nuthouse and now I'm in jail?" as he walks back into the prison.
Read more about this topic: Bottle Rocket
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