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