Derek Richardson

Harry Dunne

Eric Christian Olsen

Lloyd Christmas

Mimi Rogers

Mrs. Dunne

Luis Guzmán

Ray

Rachel Nichols

Jessica

Eugene Levy

Principal Collins

Teal Redmann

Terri

Shia LaBeouf

Lewis

Lin Shaye

Margie

Elden Henson

Turk

William Lee Scott

Carl

Michelle Krusiec

Ching Chong

Dana Gould

Mr. Moffitt

Brian Posehn

Store Clerk

Jeff Cesario

P.A. Announcer

Cheri Oteri

Ms. Heller

Bob Saget

Jessica's Dad

Timothy Stack

Doctor

Wayne Federman

Officer Dave

Holly Towne

Preppy Student

Josh Braaten

Toby

Tally Barr

Nice Jugs Girl

Julia Duffy

Jessica's Mom

Jill Talley

Mom

Roger Eschbacher

Superintendent Zimmer

Dawn Michelle King

Woman

Colin Ford

Lloyd (at age 5) (uncredited)