Kevin Smith Silent Bob Director, Actor, Writer, Film Editing Ben Affleck Holden, Ben, Chuckie Actor Jeff Anderson Randal Actor Diedrich Bader Miramax Security Guard Gordon Actor Eliza Dushku Sissy Actor Shannon Elizabeth Justice Actor Will Ferrell Willenholly Actor Mark Hamill Cock-Knocker Actor Ali Larter Chrissy Actor Jason Lee Brodie, Banky Actor Jason Mewes Jay Actor Brian O'Halloran Dante Hicks Actor Chris Rock Chaka Actor Seann William Scott Brent Actor Joey Lauren Adams Alyssa Actor Jules Asner Self Jason Biggs Self Marc Blucas The Guy Actor George Carlin Hitchhiker Actor Wes Craven Self Matt Damon Himself , Will Hunting Actor Shannen Doherty Rene Mosier Actor Carrie Fisher Nun Actor Jamie Kennedy Chaka's Production Assistant Actor Steve Kmetko Self Tracy Morgan Dealer Actor Alanis Morissette That Woman (God) Actor Judd Nelson Sheriff Actor Jennifer Schwalbach Smith Missy Actor Jon Stewart Reg Hartner Actor Scott Mosier Producer, Film Editing Bob Weinstein Executive Producer Harvey Weinstein Executive Producer Jonathan Gordon Executive Producer Laura Greenlee Co-Producer Jamie Anderson Cinematographer Robert Holtzman Production Design James L. Venable Original Music Joseph Grossberg Visual Effects Supervisor Isis Mussenden Costume Design Christine Sheaks Casting Timothy Bird First Assistant Director Elise G. Viola Art Director Jefferey Macintyre Set Decoration Douglas A. Mowat Set Decoration Ralph Meyer Location Manager