Dawson Leery

James Van Der Beek

Joey Potter

Katie Holmes

Pacey Witter

Joshua Jackson

Jennifer "Jen" Lindley

Michelle Williams

Jack McPhee

Kerr Smith

Audrey Liddell

Busy Philipps

Evelyn "Grams" Ryan

Mary Beth Peil

Gail Leery

Mary-Margaret Humes

Eddie Doling

Oliver Hudson

Guest Star

Dr. Drew Pinsky

Natasha Kelly

Bianca Kajlich

Todd Carr

Hal Ozsan

Guest Star

John Finn

Guest Star

Mimi Rogers

Matt Freeman

Sebastian Spence

Guest Star

Alicia Coppola

C.J.

Jensen Ackles

Mitch Leery

John Wesley Shipp

Guest Star

Adam Carolla

Bessie Potter

Nina Repeta

Guest Star

Greg Rikaart

Guest Star

Megan Gray

Guest Star

Geoffrey Lewis

Andie McPhee

Meredith Monroe

Guest Star

Jack Osbourne

Guest Star

Jason M. Palmer

Mike Potter

Gareth Williams

Rich Rinaldi

Dana Ashbrook

Guest Star

Roger Howarth

Female Student

Melissa Ponzio

Doug Witter

Dylan Neal

Guest Star

Mika Boorem

Head Counselor

Chandler McIntyre

Gretchen Witter

Sasha Alexander

Drue Valentine

Mark Matkevich

Co-worker #2

Johnny Alonso

Friend /Party Goer

Rease Etzler

Henry Parker

Michael Pitt

Abby Morgan

Monica Keena

Darce Florio

Charlie Todd

Chad Michael Murray

David Wilder

Ken Marino

Tamara Jacobs

Leann Hunley

Bodie Wells

Obi Ndefo

Student / Rower / Frat Guy

Edwin Modlin II

Arthur Brooks

Harve Presnell

Danny Brecher

Ian Kahn

Joseph McPhee

David Dukes

Principal Howard Green

Obba Babatundé

Tobey Barret

David Monahan

Mrs. Valentine

Carolyn Hennesy

Karen Torres

Lourdes Benedicto

Oliver Chirchick

Jordan Bridges

Chris Wolfe

Jason Behr

Marcy Bender / Sage the Anxiety Girl

Aubrey Dollar

Eric

Ryan Bittle

Mr. Milo

Richard K. Olsen

Ethan

Adam Kaufman

Mr. Kasdan

David Downs

Blossom

John Driscoll