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