Greg Kinnear

Character: Paul Duncan

Rebecca Romijn

Character: Jessie Duncan

Robert De Niro

Character: Richard Wells

Cameron Bright

Character: Adam Duncan

Zoie Palmer

Character: Susan Pierce

Munro Chambers

Character: Max Shaw

Marcia Bennett

Character: Principal Hersch

Jake Simons

Character: Dan Sandler

Devon Bostick

Character: Zachary Clark Wells

Melanie Tonello

Character: St. Pius Student

Andrew Chalmers

Character: St. Pius Student

Nancy Hochman

Character: Mrs. Baker

Merwin Mondesir

Character: Maurice, Young Thug

Sava Drayton

Character: Young Thug #2

Elle Downs

Character: Clara Sandler

Edie Inksetter

Character: Footlocker Cashier

Raoul Bhaneja

Character: Samir Miklat

Jenny Cooper

Character: Sandra Shaw

Jeff Christensen

Character: Hal Shaw

Deborah Odell

Character: Tanya

Ingrid Veninger

Character: Mrs. Farr

Tracey Hoyt

Character: Delivery Nurse

Janet Bailey

Character: Cora Williams

Thomas Chambers

Character: Jordan Shaw

Lisa Ciara

Character: Girl at the Carnival (uncredited)

Al Bernstein

Character: Godsend Receptionist