Tom Everett Scott
Josh

Mark-Paul Gosselaar
Cooper

Poppy Montgomery
Rachel

Lochlyn Munro
Cliff

Alyson Hannigan
Lucy

Randy Pearlstein
Buckley

Corey Page
Matt

Jason Segel
Kyle

Linda Cardellini
Kelly

Mari Morrow
Kristin

Aeryk Egan
Pickle

Judyann Elder
Guidance Counselor

Wynn Irwin
Sonny

John Aprea
Mr. Frederickson

Michael O'Hagan
Chemistry Professor

Nancy Linehan Charles
Anatomy Professor

Shelley Malil
Biology Professor

Paul Collins
Professor Durkheim

Daniel Villarreal
Roberto

Annie O'Donnell
Merrilee

P.J. Ochlan
Boy Bookworm

Michael Rivkin
'Shhh'-ing Student

Peter James Smith
Calculus Seatmate

Kurt Loder
Self

Mary Stein
Irritated Woman

Brian Howe
Frank

Patrick Thomas O'Brien
Priest

Rueben Grundy
Guy

Steve Mackall
TV Show Host

Cory Oliver
Pam

Zoaunne LeRoy
Cafeteria Worker

Kenn Michael
Luke

Jon Barton
Boyfriend (uncredited)