Gregory Smith

as Holden Donovan

Caitlin Wachs

as Katie Carmichael

Stephanie Sherrin

as Charlotte Pratt

Nicole Richie

as Kelly Stepford

Julie Bowen

as Principal Weller

Rosanna Arquette

as Abby Pratt

Elizabeth Perkins

as Sondra Carmichael

Samantha Mathis

as Jennifer Rose

George Wendt

as Coach Thompson

Alex Anfanger

as Lawrence Reitzer

Emy Coligado

as Emily Chua

Crystal Celeste Grant

as Walanda Jenkins

Malik Yoba

as Will Drucker

Andrew Shaifer

as Kip Stratton

Genevieve Padalecki

as Ashley Harris

Adam Arkin

as Ed Mumsford

Jeff Chase

as Asst. Coach Fasso

Tim Griffin

as Tony

Charles Shaughnessy

as Sergeant Carmichael

Rosalie Ward

as Monica Rose

W. Earl Brown

as Boss McGinn

Marcella Lentz-Pope

as Elizabeth Goings

Damien Luvara

as Rick Garcia

Leila Leigh

as Jane Jordan

Matthew Brent

as Nat French

Antoinette Peragine

as Tammy