Tim Burton
as
Brian
Jeremy Piven
as
Doug Hughley
Tom Skerritt
as
Mayor Weber
Eric Stoltz
as
The Mime
Matt Damon
as
Benjamin Mee
Thomas Haden Church
as
Duncan Mee
Scarlett Johansson
as
Kelly Foster
Elle Fanning
as
Lily Miska
Jed Rees
as
Chuck Hasboro
Kirsten Dunst
as
Claire Colburn
Judy Greer
as
Heather Baylor
Susan Sarandon
as
Hollie Baylor
Jay Mohr
as
Bob Sugar
Eric Stoltz
as
Ethan Valhere
Lucy Liu
as
Former Girlfriend
Tom Cruise
as
Jerry Maguire
Tom Cruise
as
David Aames
Ivana Milicevic
as
Emma
Steven Spielberg
as
Guest at David Aames' Party
Penélope Cruz
as
Sofia Serrano
Emma Stone
as
Allison Ng
Ivana Milicevic
as
Carson Biographer
John Krasinski
as
John 'Woody' Woodside
Rachel McAdams
as
Tracy Woodside
Adam Sandler
as
Opera Man
Johnny Depp
as
Self
Bob Dylan
as
Self
Pete Townshend
as
Self
Joan Cusack
as
Constance Dobler
John Cusack
as
Lloyd Dobler
Jeremy Piven
as
Mark
Eric Stoltz
as
Vahlere
Zooey Deschanel
as
Anita Miller
Ana Maria Quintana
as
Arizona Housekeeper
Kate Hudson
as
Penny Lane
Jay Baruchel
as
Vic Munoz