Anthony Heald

as Vice Principal Scott Guber

Chi McBride

as Principal Steven Harper

Fyvush Finkel

as Harvey Lipschultz

Nicky Katt

as Harry Senate

Jessalyn Gilsig

as Lauren Davis

Loretta Devine

as Marla Hendricks

Sharon Leal

as Marilyn Sudor

Rashida Jones

as Louisa Fenn

Joey Slotnick

as Milton Buttle

Tom McCarthy

as Kevin Riley