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