Thurgood (Chappelle) and his friends Brian (Breuer) and Scarface (Diaz) are forced into selling medical marijuana stolen from the lab where Thurgood works as a "custodian" (janitor) in order to bail their friend Kenny (Williams) out of jail, after he accidentally killed a diabetic police horse by feeding it junk food. Their business, named Mr. Nice Guy in honor of their good-natured incarcerated friend, becomes immensely popular, even attracting famous clientele. However, Thurgood's personal life is ruined once his adamantly anti-drug girlfriend, ironically named Mary Jane Potman (Rachel True), discovers that he works for Mr. Nice Guy. Soon, all of their lives are in danger once Sampson Simpson, a local drug dealer, learns that Mr. Nice Guy is costing him business, including his former client rapper Sir Smoka Lot. He threatens to kill them. Brian also buys a pouch that is supposed to contain the ashes of Jerry Garcia with all the money they are making.

However, Thurgood tells police about a meeting he has with Sampson Simpson after they arrest him for stealing marijuana from the laboratory. The police agree to drop the charges if Thurgood wears a wire, that way they can get the proof they need to arrest the druglord. During the interview Simpson discovers that Thurgood is wearing a wire and is about to kill them when Brian throws the pouch he bought earlier on the ground. Jerry Garcia comes out and hits Simpson with a guitar, knocking him out, and police rush in and recover all of the drugs, and arrest Simpson after he wakes up. Thurgood, Brian, and Scarface's deal with the police and also get Kenny a pardon from jail. Thurgood gives up smoking and is able to win back Mary Jane.

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