Gerard Butler as Milo Boyd

Jennifer Aniston as Nicole Hurley

Peter Greene as Earl Mahler

Jeff Garlin as Sid

Jason Sudeikis as Stewart

Gio Perez as Uncle Sam

Siobhan Fallon Hogan as Teresa

Joel Marsh Garland as Dwight

Jason Kolotouros as Gelman

Matt Malloy as Gary

Adam Rose as Jimmy

Christine Baranski as Kitty Hurley

Dorian Missick as Bobby Jenkins

David Costabile as Arthur

Lynda Gravatt as Judge

Charlie Hewson as Rich Guy

Charles Techman as Track Vet

Lou Sumrall as Bone

Jayne Houdyshell as Landlady

Cathy Moriarty as Irene

Ritchie Coster as Ray

Mary Testa as Maid at the Taj

Harry Zittel as Pedicab Driver

Tracy Thorne as Membership Director

Christian Borle as Caddy

Amanda Hope Dutton as Darla

Carol Kane as Dawn

Adam LeFevre as Edmund

Edward Mitchell as Jonathan

Patrick Mitchell as Jeremy

Brooke Allison as Strip Club Waitress

Eric Zuckerman as Kenny

Wally Dunn as Depository Clerk