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

Kevin Duhaney
Young Thurgood

Neal Brennan
Employee

Jenni Burke
Overweight Woman

David Mucci
Horse Cop

Kevin Rushton
Inmate

Kyrin Hall
Henchwoman

Joanna Bacalso
Henchwoman

C.J. Lusby
Henchwoman

Angelica Lisk-Hann
Henchwoman

Jacqueline Anderson
Henchwoman Delilah

Ho Chow
Hot Dog Vendor

Jon Stewart
Enhancement Smoker

Snoop Dogg
Scavenger Smoker

Stephen Baldwin
McGuyver Smoker

Tracy Morgan
V.J.

Paulino Nunes
SWAT Cop

Jason Blicker
Detective

Dave Nichols
Detective

Sharon Brown
Talking Joint

David Sutcliffe
After School Dad

Daniel DeSanto
After School Son

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)