Charlie Maguire

Ben Affleck

JR Maguire

Tye Sheridan

Young JR Maguire

Daniel Ranieri

Dorothy Maguire

Lily Rabe

Grandpa Maguire

Christopher Lloyd

The Voice/Johnny Michaels

Max Martini

Wesley

Rhenzy Feliz

Sidney

Briana Middleton

Chief

Max Casella

Grandma Maguire

Sondra James

Bobo

Michael Braun

Joey D

Matthew Delamater

Jimmy

Ivan Leung

Aunt Ruth

Danielle Ranieri

Priest

Billy Meleady

Kathy

Kate Avallone

Sydney's Dad

Mark Boyett

Sydney's Mom

Quincy Tyler Bernstine

Professor Van Dyke

Ezra Knight

School Psychologist

David Carl

Pat

Shannon Collis

Kathy's Daughter

Keira Jo Lassor

Mrs. Williams(as Jennifer Johnson)

Jennifer C. Johnson

NYT Editor

Michael Steven Costello

NYT Personnel Woman

Kate Middleton

NYT CopyBoy

Jackson Damon

NYT Copygirl

Caroline Bergwall

Chief's Wife

Jenny Eagan

Officer James

Daniel Washington

Other Customer

Steve Gagliastro

Aunt Ruth's Kid #1

Annabella Valle

Aunt Ruth's Kid #2

Clara Kelly

Aunt Ruth's Kid #3

Meara Mahoney Gross

Future JR Maguire (voice only)

Ron Livingston

Dickens Bar Regular (uncredited)

Julia Bechler

Bianca

Mellanie Hubert

Yale Student (uncredited)

Keith R. Beck

Dickens Bar Patron (uncredited)

Alissa Bourne

NYT Copyboy

Jack Damon