Will Ferrell

Phil Weston

Robert Duvall

Buck Weston

Mike Ditka

Mike Ditka

Kate Walsh

Barbara Weston

Musetta Vander

Janice Weston

Dylan McLaughlin

Sam Weston

Josh Hutcherson

Bucky Weston

Steven Anthony Lawrence

Mark Avery

Elliott Cho

Byong Sun

Erik Walker

Ambrose

Dallas McKinney

Connor

Timmy Deters

Alex

David Herman

Referee

Rachael Harris

Ann Hogan

Laura Kightlinger

Donna Jones

Jim Turner

Jim Davidson 'The Captain'

Julia Campbell

Janet Davidson

Phill Lewis

John Ryan

David Bowe

Forest Avery

Matt Winston

Tom Hanna

Susan Barnes

Diana Ditka

Lu Elrod

Patty

Tom Virtue

Track & Field Coach

Karly Rothenberg

Jack's Mother

Joseph R. Sicari

Umberto

Timm Sharp

Butcher Shop Employee

Frank Cassavetes

Butcher Shop Employee

Jarrad Paul

Beantown Employee

Rob Benedict

Beantown Employee

Martin Starr

Beantown Customer

Lisa Lackey

Beantown Customer

Brian Palermo

Beantown Customer

Scott Adsit

Stew

Peter Jason

Clark

Mason Lucero

Tarantula

Alex Borstein

Obnoxious Hummer Lady (uncredited)