Norman Wallach

F. Murray Abraham

Tom Kuftinec

Ralph Macchio

Maxine "Max" Kuftinec

Makenna Ballard

Sarah Kuftinec

Janeane Garofalo

YaYa

Olympia Dukakis

Isabella Diaz

Fatima Ptacek

Laura Langer

Kimberly Quinn

Aunt Diane

Rachel Dratch

Becky

Oona Laurence

Blackstone Head of School

Tovah Feldshuh

Jaden

Gabriel Rush

Jez Kuftinec

Fina Strazza

Mel

Franklin Ojeda Smith

Blackstone Academy Chess Club Private Schoolgirl

Giovanna Cappetta

Dream Mom

Graci Carli

Max's Classmate

Carson Allsteadt

Jessica

Catherine Urbanek

Officer

Frank Pando

Olive

Jazmin Kamali

Blackstone Academy Chess Club Member

Evie Paller

Mrs. Winter

Allyson Morgan

Mourner

Lucinda Lewis

Max 1

Jaden Michael

Chess Player

Bill Hobbs

Chess Player

And Palladino

Blackwater Private School Student

Jenna Iacono

Feature Extra

Katelynn Bailey

Pseudo Jeremy Lin

Raymond Chu

Blackstone Academy School

Savannah Janiszewski

Teacher

Janelle Anne Robinson

Chess Club Member/Classmate

Paige Cederlund

Mr. Eckhart

Terrence Gray

School Girl

Deneice O'Connor

Max 2

Ben Gibbons

Child

Jessica Styles

The Babysitter

Molly Winsten

Parasol Girl

Penelope Wendtlandt

Woman on Cell Phone

Cheri Paige Fogleman

Student-Mean Girl

Courtney Lee

Blackstone Academy Private Schoolgirl

Trinity S. Brittingham

Chess Player

Scott Martin