Tobey Maguire as David

Reese Witherspoon as Jennifer

William H. Macy as George Parker

Joan Allen as Betty Parker

Jeff Daniels as Mr. Johnson

J. T. Walsh as Big Bob

Paul Walker as Skip

Don Knotts as TV Repairman

Marley Shelton as Margaret Henderson

Jane Kaczmarek as David's Mom

Giuseppe Andrews as Howard

Jenny Lewis as Christin

Marissa Ribisi as Kimmy

Denise Dowse as Health Teacher

McNally Sagal as Science Teacher

Paul Morgan Stetler as College Counselor

Kevin Connors as Bud Parker

Natalie Ramsey as Mary Sue Parker

Justin Nimmo as Mark Davis

Kai Lennox as Mark's Lackey #1

Jason Behr as Mark's Lackey #2

Harry Singleton as Mr. Simpson

John Ganun as Fireman #1

Dawn Cody as Betty Jean

Maggie Lawson as Lisa Anne

Andrea Baker as Peggy Jane

Lela Ivey as Miss Peters

Marc Blucas as Basketball Hero

Danny Strong as Juke Box Boy

Heather McGill as Girl in School Yard

Robin Bissell as Commercial Announcer (voice)

Jim Patric as Tommy

Stanton Rutledge as Coach

Jason Maves as Paperboy

Gerald Emerick as TV Weatherman

Charles C. Stevenson Jr. as Dr. Henderson

Nancy Lenehan as Marge Jenkins

Weston Blakesley as Gus

Patrick Thomas O'Brien as Roy

Jim Antonio as Ralph

Kristin Rudrüd as Mary

Laura Carney as Bridge Club Lady

Dan Gillies as Fireman #2

Erik MacArthur as Will

Adam Carter as Boy in Soda Shop

David Tom as Whitey

Johnny Moran as Pete

Jeanine Jackson as Woman

J. Patrick Lawlor as Thug

James Keane as Police Chief Dan