Dave Chappelle

Thurgood Jenkins / Sir Smoke-a-Lot

Jim Breuer

Brian

Harland Williams

Kenny Davis

Guillermo Díaz

Scarface

Rachel True

Mary Jane Potman

Tommy Chong

Squirrel Master

Clarence Williams III

Samson Simpson

Laura Silverman

Jan

R.D. Reid

Scientist

Gregg Rogell

Pothead

Alice Poon

Supply Clerk

Rick Demas

Nasty Nate

David Bluestein

Jerry Garcia

Kevin Duhaney

Young Thurgood

Matthew Raposo

Young Scarface

Michael Colton

Young Kenny

Paul Brogren

Burger Customer

Neal Brennan

Employee

Karen Waddell

Record Store Employee

Vincent Marino

Bodega Man

Marcus Burrowes

Rasta Man

Jenni Burke

Overweight Woman

David Mucci

Horse Cop

Reg Dreger

Judge

Kevin Rushton

Inmate

Paul James Saunders

Doorman

Kyrin Hall

Henchwoman

Joanna Bacalso

Henchwoman

C.J. Lusby

Henchwoman

Angelica Lisk-Hann

Henchwoman

Jacqueline Anderson

Henchwoman Delilah

Stephanie Bourgeois

Henchwoman

Ho Chow

Hot Dog Vendor

Rummy Bishop

Homeless Guy

Jon Stewart

Enhancement Smoker

Snoop Dogg

Scavenger Smoker

Stephen Baldwin

McGuyver Smoker

Marc Cohen

McGuyver Friend

Tracy Morgan

V.J.

David Edwards

Addict

Paulino Nunes

SWAT Cop

Jason Blicker

Detective

Dave Nichols

Detective

Sharon Brown

Talking Joint

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)