Ben Affleck character Charlie Maguire
Tye Sheridan character JR Maguire
Daniel Ranieri character Young JR Maguire
Lily Rabe character Dorothy Maguire
Christopher Lloyd character Grandpa Maguire
Max Martini character The Voice, JR's father
Rhenzy Feliz character Wesley
Briana Middleton character Sidney
Max Casella character Chief
Sondra James character Grandma Maguire
Michael Braun character Bobo
Matthew Delamater character Joey D
Ivan Leung character Jimmy
Danielle Ranieri character Aunt Ruth
Kate Avallone character Kathy
Mark Boyett character Sidney's Dad
Quincy Tyler Bernstine character Sidney's Mom
Ezra Knight character Professor Van Dyke
David Carl character School Psychologist
Shannon Collis character Pat
Keira Jo Lassor character Kathy's Daughter
Jennifer C. Johnson character Mrs. Williams
Michael Steven Costello character NYT Editor
Kate Middleton character NYT Personnel Woman
Jackson Damon character NYT Copyboy
Caroline Bergwall character NYT Copygirl
Daniel Washington character Officer James
Jenny Eagan character Chief's Wife
Steve Gagliastro character Other Customer
Annabella Valle character Aunt Ruth's Kid #1
Clara Kelly character Aunt Ruth's Kid #2
Meara Mahoney Gross character Aunt Ruth's Kid #3
Ron Livingston character Future JR Maguire (voice only)
Jack Baumrind character Kid in Classroom (uncredited)
Julia Bechler character Dickens Bar Regular (uncredited)
Keith R Beck character Yale Student (uncredited)
Alissa Bourne character Dickens Bar Patron (uncredited)
