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- Dave Chappelle as Thurgood Jenkins
- Guillermo Diaz as Scarface
- Jim Breuer as Brian
- Harland Williams as Kenny Davis
- Clarence Williams III as Samson Simpson
- Rachel True as Mary Jane Potman
- Laura Silverman as Jan
- Tommy Chong as Squirrel Master
- Willie Nelson as Historian Smoker
- Tracy Morgan as V.J.
- Snoop Dogg as Scavenger Smoker
- Jon Stewart as Enhancement Smoker
- Stephen Baldwin as MacGyver Smoker
- Steven Wright as The Guy on the Couch
- Bob Saget as Cocaine Addict
- Janeane Garofalo as "I'm Only Creative When I Smoke" Smoker