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| Directed by | ||
|---|---|---|
 | Tamra Davis | |
| Starring | ||
|---|---|---|
 | Adam Sandler | Billy Madison |
 | Darren McGavin | Brian Madison |
| Bridgette Wilson-Sampras | Veronica Vaughn |
| Bradley Whitford | Eric Gordon |
| Josh Mostel | Principal Max Anderson |
| Norm MacDonald | Frank |
| Mark Beltzman | Jack |
| Larry Hankin | Carl Alphonse |
| Theresa Merritt | Juanita |
| Dina Platias | Miss Lippy |
| Hrant Alianak | Pete |
| Vincent Marino | Cook |
| Jack Mather | Ted 'Old Man' Clemens |
| Christopher Kelk | Rollo the Janitor |
| Marc Donato | Nodding 1st Grader |
| Keith Cole | Penguin |
| Chris Mei | Penguin |
| Conor Devitt | O'Doyle (Grade 1) |
| Jared Durand | Scotty Logan (Grade 1) |
| Jessica Nakamura | Tricia Labonte (Grade 1) |
| Helen Hughes | 2nd Grade Teacher |
| Jacelyn Holmes | 2nd Grader |
| Claire Cellucci | Attractive Lady |
| Shane Farberman | Clown |
| Al Maini | Chauffeur |
| Jared Cook | Ernie (Grade 3) |
| Christian Matheson | O'Doyle (Grade 3) |
| Kyle Bailey | Kyle |
| Vernon Chapman | Butler |
| Mandy Watts | Maid |
| Austin Pool | Dan (Grade 3) |
| Gladys O'Connor | Tour Guide |
| Marcia Bennett | 4th Grade Teacher |
| Diane Douglass | Nurse |
| Tim Herlihy | Architect |
| Frank Nakashima | Architect |
| Joyce Gordon | Lunch Lady |
| Jordan Lerner-Ellis | Pothead |
| Daniel Lerner-Ellis | Pothead |
| Robert Smigel | Mr. Oblaski |
| Melissa Korzenko | Nancy Connors |
| Colin Smith | O'Doyle (Grade 9) |
| Jeff Moser | Paul |
| Amos Crawley | Rod |
| Tex Konig | Crazy Persons |
| Eduardo Gomez | Crazy Persons |
| Tanya Grout | Joyce (Eric's Sercetary) |
| Benjamin Barrett | Tenth Grader |
| Matthew Ferguson | Tenth Grader |
| Sean Lett | O'Doyle (Grade 12) |
| Stacey Wheal | Jennifer (Grade 3) |
| Shanna Bresee | Susan (Grade 3) |
| Michael Ayoub | Drama Teacher |
| Lawrence Nakamura | Lawn Guy |
| Gino Veltri | Rock Singer |
| James Downey | Principal |
| Bob Rodgers | Mr. O'Doyle |
| Margo Wladyka | Mrs. O'Doyle |
| Allison Robinson | Newswoman |
| Marcel Jean Gilles | Haitian Gardener |
| Suzanna Shebib | High School Girl |
| Justin Williams | 3rd Grader |
| Nicholas A. Catalano | 3rd Grader |
| Devon Codrington | 3rd Grader |
| Nicole Harrison | 3rd Grader |
| Lindsay Curran | 3rd Grader |
| Brandi Tower | 3rd Grader |
| Cassandra Forrester | 3rd Grader |
| Matthew Tempest | 3rd Grader |
| Michelle Toth | 3rd Grader |
| Craig MacIsaac | 3rd Grader |
| Tara Rooney | 3rd Grader |
| Robby Cavallari | 3rd Grader |
| Ryan Luis | 3rd Grader |
| Alanna Budhoo | 3rd Grader |
| Shomar Dejonge | 3rd Grader |
| Carmela Bigioni | 3rd Grader |
| Eric Aguilera | 3rd Grader |
| Kevin Le Roy | Jet Skier |
| Kelly Childerhose | Jet Skier |
| Ken Shires | Fire-eater |
| Steve Buscemi | Danny McGrath |
| Chris Farley | Bus Driver |
| Jordan-Patrick Marcantonio | 10th Grader |
| John Yost | Brian's Business Associates #1 |
5th July 2020
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