Hilary Duff as Sam Montgomery

Chad Michael Murray as Austin Ames

Jennifer Coolidge as Fiona

Dan Byrd as Carter Farrell

Regina King as Rhonda

Julie Gonzalo as Shelby Cummings

Lin Shaye as Mrs. Wells

Madeline Zima as Brianna

Andrea Avery as Gabriella

Mary Pat Gleason as Eleanor

Paul Rodríguez as Bobby

Whip Hubley as Sam's Dad

Kevin Kilner as Austin's Dad

Erica Hubbard as Madison

Simon Helberg as Terry

Brad Bufanda as David

J. D. Pardo as Ryan

Aimee-Lynn Chadwick as D.J.

Kady Cole as Caitlyn

Hannah Robinson as Young Sam

Josh Prince as Swim Coach

Art LaFleur as Coach

James Eckhouse as Mr. Farrell

Jonathan Slavin as Vernon

John Billingsley as Mr. Rothman

Lilli Babb as Young Gabriella

Carlie Westerman as Young Brianna

Mike Randleman as Chuck

Christie Herring as Bachelorette #1

Lindsay Hollister as Bachelorette #2

Taylor Hoover as Beautiful Bachelorette

Brittany Weber as Bachelorette

Darryl Sivad as District Attorney

Rita Maye Bland as Rollerskating Waitress #1

Keli Murphy as Rollerskating Waitress #2

Alexis Raich as Girl at Carwash

Sabin Rich as Locker Guy

Sandra McCoy as Cheerleader / Dancer #1

Julianne Waters as Cheerleader / Dancer #2

Karen Elmore as Cheerleader / Dancer #3

Stella Choe as Cheerleader / Dancer #4

Jessie Rice-Holiday as Cheerleader / Dancer #5

Cricket Hamar as Cheerleader / Dancer #6

Shannon Novak as Cheerleader / Dancer #7

Oscar Orosco as Fighting Frog Mascot

Jason Beitel as Halloween Dancer

Kato Bonner as Hallwoeen Dancer

Carol Borjas as Halloween Dancer

Reshma Gajjar as Halloween Dancer

Molly Gosline as Halloween Dancer

Hunter Hamilton as Halloween Dancer

Richy Jackson as Halloween Dancer

Trey Knight as Halloween Dancer

Jonathan Ritter as Halloween Dancer

Jenny Seeger as Halloween Dancer

Becca Sweitzer as Halloween Dancer

Melanie A. Gage as Dancer

Jolene Riella as Dancer

Elle Beyer as Waitress

Joe Jagatic as Wedding Photographer

Lon Beyer as Waiter

Tarah Paige as Dancer

Justin Rhoads as Student in Bleachers

Danielle Riffenburgh as Go-Go Dancer

Rory Thost as Young Carter Farrell

John H. Tobin as Dad at Carwash

Toni Wynne as Kitty