Tom Everett Scott as Josh

Mark-Paul Gosselaar as Cooper

Poppy Montgomery as Rachel

Lochlyn Munro as Cliff

Alyson Hannigan as Lucy

Randy Pearlstein as Buckley

Corey Page as Matt

Jason Segel as Kyle

Linda Cardellini as Kelly

Mari Morrow as Kristin

Mark Carapezza as Hank

Jeff Tarpley as Jerry

Aeryk Egan as Pickle

Judyann Elder as Guidance Counselor

Dave Ruby as Zeke

Wynn Irwin as Sonny

John Aprea as Mr. Frederickson

Michael O'Hagan as Chemistry Professor

Nancy Linehan Charles as Anatomy Professor

Shelley Malil as Biology Professor

Ann Fairlie as Mrs. Boison

Paul Collins as Professor Durkheim

Johnny Dark as Henry The Drunk

Daniel Villarreal as Roberto

Annie O'Donnell as Merrilee

P.J. Ochlan as Boy Bookworm

Michael Rivkin as 'Shhh'-ing Student

Peter James Smith as Calculus Seatmate

Kurt Loder as Self

Mary Stein as Irritated Woman

Brian Howe as Frank

Patrick Thomas O'Brien as Priest

Rueben Grundy as Guy

Steve Mackall as TV Show Host

Cory Oliver as Pam

Zoaunne LeRoy as Cafeteria Worker

Kenn Michael as Luke

Tracey Stone as Girl Groupie

Jon Barton as Boyfriend (uncredited)