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| Trevor Fehrman | Handsome Davis |
| Elden Henson | Sammy Green |
| Matthew Lawrence | Victor Barone |
| Martin Starr | Jonathan Jacob Applebee the Crib Master |
| Griffin Dunne | Mr. Davis, Handsome's Father |
| Maggie Lawson | Julie Merkel |
| Mary Tyler Moore | Mrs. Stark, Principal |
| David Krumholtz | Evan Rosengarden |
| Jewel Staite | Teddy Blue the Teacher Curser |
| Shayn Solberg | Lebo |
| Will Sanderson | Rexler the Jock |
| Morris Panych | Mr. Alex Harkin |
| Chang Tseng | Marty the Janitor |
| Barbara Tyson | Mrs. Herman the "Grade Book" |
| Kathryn Anderson | 2nd Grade Teacher |
| Jay Brazeau | Dr. Fox (uncredited) |
| Dixon Cohee | Greedy Herman |
| Casey Dubois | Handsome Davis - 2nd Grade |
| Leonie Haworth | Julie Merkel - 2nd Grade |
| Brandy Heidrick | Hot Highschool Girl #1 |
| Marcus Hondro | Homeless Guy (uncredited) |
| P.J. Johal | Highschool Student |
| Andrew Johnston | Dr. Newman (uncredited) |
| Aaron Joseph | Kid (uncredited) |
| Brett Kelly | Young Sammy |
| Eliza Murbach | Noga |
| Lachlan Murdoch | Horny Herman |
| Douglas Newell | Proctor |
| Tania Saulnier | Hot Highschool Girl #2 |
Four friends deceive authority figures in order to make it through high school.
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