Dave Chappelle

Character: Thurgood Jenkins / Sir Smoke-a-Lot

Jim Breuer

Character: Brian

Harland Williams

Character: Kenny Davis

Guillermo Díaz

Character: Scarface

Rachel True

Character: Mary Jane Potman

Tommy Chong

Character: Squirrel Master

Clarence Williams III

Character: Samson Simpson

Laura Silverman

Character: Jan

R.D. Reid

Character: Scientist

Gregg Rogell

Character: Pothead

Kevin Brennan

Character: Pothead

Alice Poon

Character: Supply Clerk

Rick Demas

Character: Nasty Nate

David Bluestein

Character: Jerry Garcia

Kevin Duhaney

Character: Young Thurgood

Matthew Raposo

Character: Young Scarface

James Cooper

Character: Young Brian

Michael Colton

Character: Young Kenny

Paul Brogren

Character: Burger Customer

Neal Brennan

Character: Employee

Karen Waddell

Character: Record Store Employee

Vincent Marino

Character: Bodega Man

Domencio 'Macio' Parrilla

Character: Rasta Man

Marcus Burrowes

Character: Rasta Man

Mark Henriques

Character: Delivery Guy

Jenni Burke

Character: Overweight Woman

David Mucci

Character: Horse Cop

Reg Dreger

Character: Judge

Kevin Rushton

Character: Inmate

Paul James Saunders

Character: Doorman

Kyrin Hall

Character: Henchwoman

Joanna Bacalso

Character: Henchwoman

C.J. Lusby

Character: Henchwoman

Angelica Lisk-Hann

Character: Henchwoman

Jacqueline Anderson

Character: Henchwoman Delilah

Stephanie Bourgeois

Character: Henchwoman

Ho Chow

Character: Hot Dog Vendor

Rummy Bishop

Character: Homeless Guy

Jon Stewart

Character: Enhancement Smoker

Snoop Dogg

Character: Scavenger Smoker

Stephen Baldwin

Character: McGuyver Smoker

Marc Cohen

Character: McGuyver Friend

Tracy Morgan

Character: V.J.

David Edwards

Character: Addict

Paulino Nunes

Character: SWAT Cop

Jason Blicker

Character: Detective

Dave Nichols

Character: Detective

Sharon Brown

Character: Talking Joint

Christopher Mugglebee

Character: Security Guard

Raymond Hinton

Character: Security Guard

David Sutcliffe

Character: After School Dad

Daniel DeSanto

Character: After School Son

Gladys O'Connor

Character: Grandma Smoker

Willie Nelson

Character: Historian Smoker

Janeane Garofalo

Character: I'm Only Creative When I Smoke Smoker (uncredited)

Bob Saget

Character: Cocaine Addict (uncredited)

Steven Wright

Character: The Guy on the Couch (uncredited)