Tobey Maguire

David

Reese Witherspoon

Jennifer

William H. Macy

George Parker

Joan Allen

Betty Parker

Jeff Daniels

Mr. Johnson

J. T. Walsh

Big Bob

Paul Walker

Skip

Don Knotts

TV Repairman

Marley Shelton

Margaret Henderson

Jane Kaczmarek

David's Mom

Giuseppe Andrews

Howard

Jenny Lewis

Christin

Marissa Ribisi

Kimmy

Denise Dowse

Health Teacher

McNally Sagal

Science Teacher

Paul Morgan Stetler

College Counselor

Kevin Connors

Bud Parker

Natalie Ramsey

Mary Sue Parker

Justin Nimmo

Mark Davis

Kai Lennox

Mark's Lackey #1

Jason Behr

Mark's Lackey #2

Harry Singleton

Mr. Simpson

John Ganun

Fireman #1

Dawn Cody

Betty Jean

Maggie Lawson

Lisa Anne

Andrea Baker

Peggy Jane

Lela Ivey

Miss Peters

Marc Blucas

Basketball Hero

Danny Strong

Juke Box Boy

Heather McGill

Girl in School Yard

Robin Bissell

Commercial Announcer (voice)

Jim Patric

Tommy

Stanton Rutledge

Coach

Jason Maves

Paperboy

Gerald Emerick

TV Weatherman

Charles C. Stevenson Jr.

Dr. Henderson

Nancy Lenehan

Marge Jenkins

Weston Blakesley

Gus

Patrick Thomas O'Brien

Roy

Jim Antonio

Ralph

Kristin Rudrüd

Mary

Laura Carney

Bridge Club Lady

Dan Gillies

Fireman #2

Erik MacArthur

Will

Adam Carter

Boy in Soda Shop

David Tom

Whitey

Johnny Moran

Pete

Jeanine Jackson

Woman

J. Patrick Lawlor

Thug

James Keane

Police Chief Dan