Holden/Ben/Chuckie

Ben Affleck

Jay

Jason Mewes

Silent Bob

Kevin Smith

Randal

Jeff Anderson

Miramax Security Guard Gordon

Diedrich Bader

Justice

Shannon Elizabeth

Sissy

Eliza Dushku

Marshal Willenholly

Will Ferrell

Chrissy

Ali Larter

Missy

Jennifer Schwalbach

Cock-Knocker

Mark Hamill

Brent

Seann William Scott

Brodie Bruce / Banky Edwards

Jason Lee

Hitchhiker

George Carlin

Chaka Luther King

Chris Rock

Dante Hicks

Brian Christopher O'Halloran

Nun

Carrie Fisher

Chaka's Production Assistant

Jamie Kennedy

Sheriff

Judd Nelson

Alyssa Jones

Joey Lauren Adams

Pumpkin Escobar

Tracy Morgan

Tricia Jones

Renée Humphrey

Himself / Will Hunting

Matt Damon

Himself

Scott William Winters

Jules Asner

Jules Asner

Jason Biggs

Jason Biggs

Rene Mosier

Shannen Doherty

The Guy

Marc Blucas

Himself

Morris Day

Wes Craven

Wes Craven

Reg Hartner

Jon Stewart

Dude

Matthew James

Himself

James Van Der Beek

Gus Van Sant

Gus Van Sant

Steve Kmetko

Steve Kmetko

Silent Bob's Mother

Amy Noble

Jay's Mother

Ever Carradine

Pizza Delivery Guy

Joe Quesada

That Woman (God)

Alanis Morissette

Baby Silent Bob

Harley Quinn Smith

The Kid In The Helmet

Steven Anthony Lawrence

Adam Carolla

Redhead Beauty

Carmen Llywelyn

Passerby

John Willyung

Teen No. 1

Jake Richardson

Teen No. 2

Nicholas Fehlinger

Customer

Vincent Pereira

Hooper

Dwight Ewell

Cop

Ernest O'Donnell

Bookish Girl

Jane Silvia

Beauty

Carmen Llywellyn

Deputy

Dan Etheridge

Cop No. 1

Eric Winzenried

Cop No. 2

Jonathan Gordon

Cop No. 3

John Maynard

Cop No. 4

Robert H. Holtzman

Cop No. 5

Tom Dorfmeister

Suzanne

Tango

Hooker No. 1

Michelle Anne Johnson

Hooker No. 2

Merritt Hicks

`GWH2' A.D.

Scott Mosier

`GWH2' Clapper-Loader

James J. McLaughlin

`Bluntman & Chronic' A.D.

Joseph D. Reitman

`Bluntman & Chronic' Clapper-Loader

Paul Dini

William Dusky

Quentin Wright

Suburban Kid

Gregory Owen

Receptionist

Ralph Meyer

Walter Flanagan

Steve/Dave

Bryan Johnson

Alyssa

Joey Lauren Adams*

Brian Lynch

David Mandel

Director

Kevin Smith