Bobby has ties to the local mafia boss, Max, but works as an honest mason for Max's construction projects. He fights in amateur boxing matches on the side, but his career is lackluster. Struggling to support his stripper girlfriend Jessica and her daughter Chloe, Bobby decides to do a mafia job for Max. Against his better judgment, he brings his ne'er-do-well friend Ricky along.
Bobby and Ricky go to New York to act as Max's representatives for a money laundering deal with his east coast partner, Ruiz. They meet Jimmy, who will be their driver, and Horrace, who is connected to both Max and Ruiz. Ricky and Bobby squabble throughout their trip as Ricky tries to live large while Bobby wants to keep cautious and stick to the letter of Max's instructions. Ruiz has a low opinion of the pair, but sends them off to show his criminal contact, the Welshman, a good time. Gaffing several times along the way, the pair eventually manages to arrange a deal between Ruiz and the Welshman's Westie contacts.
Ricky grows suspicious of Ruiz and insists that they bring a gun to their meeting with the Westies. Bobby adamantly refuses. On the day of the meet, Ricky has disappeared, but Jimmy insists that Bobby carry on with the meeting. As Bobby begins to grow suspicious of Jimmy, he meets with the Welshman and the Westies. The Westies doublecross Bobby and the Welshman, but Ricky arrives from a side entrance with a gun. A Westie recognizes Ricky's weapon as a starter pistol and a fight breaks out. Jimmy arrives with a real pistol and sends the boys away while he deals with the Westies. Back in Los Angeles, Bobby severs all business ties with Max. Arriving home, he discovers Jessica in bed with a client and snorting cocaine. Bobby tries to convince Jessica to clean up her act for Chloe's sake, but Jessica refuses. Instead, she asks that Bobby take custody of Chloe and leave. In an epilogue set at Chuck E. Cheese's, we learn that Bobby and Ricky are now raising Chloe together -- although the two friends still bicker constantly.