Dave Chappelle
Thurgood Jenkins / Sir Smoke-a-Lot
Harland Williams
Kenny Davis
Rachel True
Mary Jane Potman
Tommy Chong
Squirrel Master
Clarence Williams III
Samson Simpson
David Bluestein
Jerry Garcia
Kevin Duhaney
Young Thurgood
Matthew Raposo
Young Scarface
Michael Colton
Young Kenny
Paul Brogren
Burger Customer
Karen Waddell
Record Store Employee
Domencio 'Macio' Parrilla
Rasta Man
Mark Henriques
Delivery Guy
Jenni Burke
Overweight Woman
Paul James Saunders
Doorman
Angelica Lisk-Hann
Henchwoman
Jacqueline Anderson
Henchwoman Delilah
Stephanie Bourgeois
Henchwoman
Jon Stewart
Enhancement Smoker
Snoop Dogg
Scavenger Smoker
Stephen Baldwin
McGuyver Smoker
Marc Cohen
McGuyver Friend
Sharon Brown
Talking Joint
Christopher Mugglebee
Security Guard
Raymond Hinton
Security Guard
David Sutcliffe
After School Dad
Daniel DeSanto
After School Son
Gladys O'Connor
Grandma Smoker
Willie Nelson
Historian Smoker
Janeane Garofalo
I'm Only Creative When I Smoke Smoker (uncredited)
Bob Saget
Cocaine Addict (uncredited)
Steven Wright
The Guy on the Couch (uncredited)