Dave Chappelle as Thurgood Jenkins / Sir Smoke-a-Lot

Jim Breuer as Brian

Harland Williams as Kenny Davis

Guillermo Díaz as Scarface

Rachel True as Mary Jane Potman

Tommy Chong as Squirrel Master

Clarence Williams III as Samson Simpson

Laura Silverman as Jan

R.D. Reid as Scientist

Gregg Rogell as Pothead

Kevin Brennan as Pothead

Alice Poon as Supply Clerk

Rick Demas as Nasty Nate

David Bluestein as Jerry Garcia

Kevin Duhaney as Young Thurgood

Matthew Raposo as Young Scarface

James Cooper as Young Brian

Michael Colton as Young Kenny

Paul Brogren as Burger Customer

Neal Brennan as Employee

Karen Waddell as Record Store Employee

Vincent Marino as Bodega Man

Domencio 'Macio' Parrilla as Rasta Man

Marcus Burrowes as Rasta Man

Mark Henriques as Delivery Guy

Jenni Burke as Overweight Woman

David Mucci as Horse Cop

Reg Dreger as Judge

Kevin Rushton as Inmate

Paul James Saunders as Doorman

Kyrin Hall as Henchwoman

Joanna Bacalso as Henchwoman

C.J. Lusby as Henchwoman

Angelica Lisk-Hann as Henchwoman

Jacqueline Anderson as Henchwoman Delilah

Stephanie Bourgeois as Henchwoman

Ho Chow as Hot Dog Vendor

Rummy Bishop as Homeless Guy

Jon Stewart as Enhancement Smoker

Snoop Dogg as Scavenger Smoker

Stephen Baldwin as McGuyver Smoker

Marc Cohen as McGuyver Friend

Tracy Morgan as V.J.

David Edwards as Addict

Paulino Nunes as SWAT Cop

Jason Blicker as Detective

Dave Nichols as Detective

Sharon Brown as Talking Joint

Christopher Mugglebee as Security Guard

Raymond Hinton as Security Guard

David Sutcliffe as After School Dad

Daniel DeSanto as After School Son

Gladys O'Connor as Grandma Smoker

Willie Nelson as Historian Smoker

Janeane Garofalo as I'm Only Creative When I Smoke Smoker (uncredited)

Bob Saget as Cocaine Addict (uncredited)

Steven Wright as The Guy on the Couch (uncredited)