Ben Affleck Charlie Maguire
George Clooney Director, Producer
Christopher Lloyd Grandpa Maguire
Max Casella Chief
Tye Sheridan JR Maguire
Lily Rabe Dorothy Maguire
Max Martini The Voice, JR's father
Rachel Tenner Casting
Ron Livingston Future JR Maguire (voice only)
Meara Mahoney Gross Aunt Ruth's Kid #3
Briana Middleton Sidney
Grant Heslov Producer
Rhenzy Feliz Wesley
Caroline Bergwall NYT Copygirl
Jon Title Sound Designer
Bryan Felty Art Direction
Jennifer C. Johnson Mrs. Williams
Martin Ruhe Director of Photography
William Monahan Screenplay
Jackson Damon NYT Copyboy
Ezra Knight Professor Van Dyke
Dara Taylor Original Music Composer
Barbara A. Hall Executive Producer
Steve Gagliastro Other Customer
Jenny Eagan Costume Design, Chief's Wife
Kalina Ivanov Production Design
Shannon Collis Pat
Ivan Leung Jimmy
Kate Middleton NYT Personnel Woman
Quincy Tyler Bernstine Sidney's Mom
Mark Boyett Sidney's Dad
Nancy Nugent Title Supervising Sound Editor
Alissa Bourne Dickens Bar Patron (uncredited)
Todd Beckett Sound Re-Recording Mixer
Kate Avallone Kathy
Sondra James Grandma Maguire
Julian Slater Supervising Sound Editor
Daniel Washington Officer James
Daniel Ranieri Young JR Maguire
Ted Hope Producer
Matthew Delamater Joey D
Michael Braun Bobo
Linda Cohen Music Supervisor
Julia Bechler Dickens Bar Regular (uncredited)
Michael Steven Costello NYT Editor
Matt Kasmir Visual Effects Supervisor
Tanya Swerling Editor
Trish Seeney Makeup Department Head
J.R. Moehringer Executive Producer, Book
Annabella Valle Aunt Ruth's Kid #1
Keith R. Beck Yale Student (uncredited)
David Carl School Psychologist
Dana Pacheco Costume Supervisor
Melissa M. Levander Set Decoration
Clara Kelly Aunt Ruth's Kid #2
Jack Baumrind Kid in Classroom (uncredited)
Danielle Ranieri Aunt Ruth
Keira Jo Lassor Kathy's Daughter