Dave Chappelle .... Thurgood Jenkins/Sir Smoke-a-Lot Guillermo Díaz .... Scarface Jim Breuer .... Brian Harland Williams .... Kenny Davis Rachel True .... Mary Jane Potman Clarence Williams III .... Samson Simpson Laura Silverman .... Jan Tommy Chong .... Squirrel Master R.D. Reid .... Scientist Gregg Rogell .... Pothead Kevin Brennan .... Pothead Alice Poon .... Supply Clerk Rick Demas .... Nasty Nate David Bluestein .... Jerry Garcia