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