Billy Madison: Um Herdeiro Bobalhão
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Adam SandlerBilly Madison
Bradley WhitfordEric Gordon
Josh MostelPrincipal Max Anderson
Bridgette Wilson-SamprasVeronica Vaughn
Darren McGavinBrian Madison
Norm MacdonaldFrank
Mark BeltzmanJack
Larry HankinCarl Alphonse
Theresa MerrittJuanita
Dina PlatiasMiss Lippy
Hrant AlianakPete- Vincent MarinoCook
- Christopher KelkRollo the Janitor
Marc DonatoNodding 1st Grader- Keith ColePenguin
- Chris MeiPenguin
- Conor DevittO'Doyle (Grade 1)
- Jared DurandScotty Logan (Grade 1)
- Jessica NakamuraTricia Labonte (Grade 1)
- Helen Hughes2nd Grade Teacher
Jacelyn Holmes2nd Grader- Jack MatherTed 'Old Man' Clemens
- Claire CellucciAttractive Lady
- Shane FarbermanClown
- Al MainiDriver
- Jared CookErnie (Grade 3)
- Christian MathesonO'Doyle (Grade 3)
- Kyle BaileyKyle
- Vernon ChapmanButler
- Mandy WattsMaid
- Austin PoolDan (Grade 3)
- Gladys O'ConnorTour Guide
Marcia Bennett4th Grade Teacher- Diane DouglassNurse
Tim HerlihyArchitect- Frank NakashimaArchitect
Joyce GordonLunch Lady- Jordan Lerner-EllisPothead
- Daniel Lerner-EllisPothead
Robert SmigelMr. Oblaski- Melissa KorzenkoNancy Connors
- Colin SmithO'Doyle (Grade 9)
- Jeff MoserPaul
Amos CrawleyRod- Tex KonigCrazy Person
- Eduardo GómezCrazy Person
Tanya GrantJoyce- Benjamin BarrettTenth Grader
Matthew FergusonTenth Grader- Sean LettO'Doyle (Grade 12)
- Stacey WhealJennifer (Grade 3)
- Shanna BreseeSusan (Grade 3)
Michael AyoubDrama Teacher- Lawrence NakamuraLawn Guy
- Gino VeltriRock Singer
Jim DowneyPrincipal- Bob RodgersMr. O'Doyle
- Margo WladykaMrs. O'Doyle
- Allison RobinsonNewswoman
- Marcel Jean GillesHaitian Gardener
- Suzanna ShebibHigh School Girl
- Justin Williams3rd Grader
- Nicholas A. Catalano3rd Grader
- Devon Codrington3rd Grader
- Nicole Harrison3rd Grader
- Lindsay Curran3rd Grader
- Brandi Tower3rd Grader
- Cassandra Forrester3rd Grader
- Matthew Tempest3rd Grader
- Michelle Toth3rd Grader
- Craig MacIsaac3rd Grader
- Tara Rooney3rd Grader
- Robby Cavallari3rd Grader
- Ryan Luis3rd Grader
- Alanna Budhoo3rd Grader
- Shomar Dejonge3rd Grader
- Carmela Bigioni3rd Grader
- Eric Aguilera3rd Grader
- Kevin Le RoyJet Skier
- Kelly ChilderhoseJet Skier
- Ken ShiresFire-eater
Steve BuscemiDanny McGrath (sem créditos)
Chris FarleyBus Driver (sem créditos)