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| Ben Affleck | Holden/Ben/Chuckie |
| Jeff Anderson | Randal |
| Diedrich Bader | Miramax Security Guard Gordon |
| Eliza Dushku | Sissy |
| Shannon Elizabeth | Justice |
| Will Ferrell | Willenholly |
| Mark Hamill | Cock-Knocker |
| Ali Larter | Chrissy |
| Jason Lee | Brodie/Banky |
| Jason Mewes | Jay |
| Brian Christopher O'Halloran | Dante Hicks |
| Chris Rock | Chaka |
| Seann William Scott | Brent |
| Kevin Smith | Silent Bob |
| Joey Lauren Adams | Alyssa |
| Jules Asner | Herself |
| Jason Biggs | Himself |
| Marc Blucas | The Guy |
| George Carlin | Hitchhiker |
| Wes Craven | Himself |
| Matt Damon | Himself / Will Hunting |
| Shannen Doherty | Rene Mosier |
| Carrie Fisher | Nun |
| Jamie Kennedy | Chaka's Production Assistant |
| Steve Kmetko | Himself |
| Tracy Morgan | Dealer |
| Alanis Morissette | That Woman (God) |
| Judd Nelson | Sheriff |
| Jennifer Schwalbach | Missy |
| Jon Stewart | Reg Hartner |
Two slackers venture to Hollywood to sabotage the production of a new movie based on their alter egos.
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