Dave Chappelle plays Thurgood Jenkins, also known as Sir Smoke-a-Lot, the protagonist who turns to selling marijuana to raise money to get his friend out of jail.
Jim Breuer portrays Brian, one of Thurgood's close friends who joins him in his pot-selling escapades.
Harland Williams takes on the role of Kenny Davis, another friend who gets involved in the group's misadventures.
Guillermo Díaz plays Scarface, a drug dealer who becomes a rival to Thurgood and his friends.
Rachel True is Mary Jane Potman, a love interest for one of the characters who shares their passion for marijuana.
Tommy Chong appears as Squirrel Master, a seasoned pot smoker who provides guidance to Thurgood and his friends.
Clarence Williams III plays Samson Simpson, an elderly man who unintentionally consumes a potent batch of marijuana.
Laura Silverman portrays Jan, a character who works alongside the group as they navigate their marijuana-related shenanigans.
R.D. Reid appears as the Scientist, a minor character involved in a scene where the group experiments with marijuana strains.
Gregg Rogell plays a Pothead, providing comedic moments as one of the individuals enjoying the group's marijuana supply.
Kevin Brennan also appears as a Pothead, adding to the comedic antics surrounding the characters' marijuana use.
Alice Poon portrays the Supply Clerk, a character involved in a humorous sequence where the group attempts to purchase marijuana supplies.
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