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