Chyler Leigh as Janey Briggs

Chris Evans as Jake Wyler

Jaime Pressly as Priscilla

Eric Christian Olsen as Austin

Mia Kirshner as Catherine Wyler

Deon Richmond as Malik

Eric Jungmann as Ricky Lipman

Ron Lester as Reggie Ray

Cody McMains as Mitch Briggs

Sam Huntington as Ox

JoAnna Garcia Swisher as Sandy Sue

Lacey Chabert as Amanda Becker

Samm Levine as Bruce

Cerina Vincent as Areola

Beverly Polcyn as Sadie Agatha Johnson

Ed Lauter as The Coach

Paul Gleason as Richard Vernon

Mr. T as The Wise Janitor

Molly Ringwald as Flight Attendant

Randy Quaid as Mr. Briggs

Samaire Armstrong as Kara Fratelli

Nectar Rose as Sara Fratelli

Riley Smith as Les

Nathan West as Actor

Michelle Holgate as Actress

Jeanette Miller as Grandma Briggs

Michael Ensign as Father O'Flannagan

Benjamin Waldow as Kid

Josh Radnor as Tour Guide

Ross Mulholland as Cheerleader in Front of School

Dean Sheremet as Cheerleader in Front of School

Becca Sweitzer as Cheerleader in Front of School

Hayley Zelniker as Cheerleader in Front of School

Lukas Behnken as White Guy

Josh Jacobson as White Guy

Amber Goetz as Window Girl

Joy Bisco as Ashley

Morisa Taylor Kaplan as Heather

George Wyner as Mr. Cornish

Ned Brower as Dude

Peter Simon as Dude

Joy Gohring as Albino Folk Singer

Tracy Kay as Hottie

Jessica Asher as Naked Girl in Locker Room

Sean Smith as Mr. Keller

Heather Brown as Dainty Girl

Ean Mering as Marty

Lyman Ward as Mr. Wyler

Julie Welch as Mrs. Wyler

Daniel Bess as Panicked Student

Jackie Harris Greenberg as Preston's Mother

James Read as Preston's Father

Rob Benedict as Preston Wasserstein

Banks McClintock as Keg Guy

Jay Johnston as Roadie

Jesse Capelli as Naked Girl at Party

Daniel Spink as Curious Guy

Osgood Perkins as Uninterested Guy

Kyle Cease as Slow Clapper

Jim Wise as Football Announcer

Kimi Bateman as Cheerleader on Football Field

Staci B. Flood as Cheerleader on Football Field

Sarah Christine Smith as Cheerleader on Football Field

China Shavers as North Compton Cheerleader

H. Jon Benjamin as Trainer

Paul Goebel as Fat Short Order Cook

Joel Madden as Prom Band

Benji Madden as Prom Band

Billy Martin as Prom Band

Marissa Fedele as Dancer

Samuel Givens as Dancer

Kimberly Lyon as Dancer

Zachary Woodlee as Dancer

Alec Murdock as Man in Line

Cynthena Sanders as Woman in Line

Will Gill Jr. as Security Guard

Nick Zephyrin as Little Boy

Kelly S. King as Art Student (uncredited)

Sean Patrick Thomas as Black Guy at Party (uncredited)

Desi Lydic as Cutie (uncredited)

Nick Bakay as Diner Cook (uncredited)

Arturo Elizondo as DJ Arte (uncredited)

Susan Anne Wall as Flight Attendant (uncredited)

Scott Hislop as Footloose Guy (uncredited)

Tracey McCall as Locker Room Girl (uncredited)

Maylen Calienes as Locker Student (uncredited)

Jeremiah Vaughn as Marty's Buddy (uncredited)

Heidi Androl as Molly (uncredited)

Sam Ayers as Paramedic (uncredited)

Gena Shaw as Party Girl (uncredited)

Jarrett Lennon as Partygoer (uncredited)

Candice T. Cain as Pom Pom Girl #3 (uncredited)

Melissa Joan Hart as Slow Clapper's Instructor (uncredited)

Tessa as Slutty Girl-New Student (uncredited)

Cassie Townsend as Student (uncredited)

Ian Aronson as Student (uncredited)

David M. Francis as Student (uncredited)

Jennifer Schlueter as Student (uncredited)

Marcus Edward as Teen with Drink at Party (uncredited)