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