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