- Becky Ann Baker - Jean Weir
- Kristy Wu - Mousy Girl
- Kevin Ruf - Police Officer
- Mike White - Chip Kelly
- Paul Feig - Alex the Guitarist
- Omri Katz - Brad
- Kevin Corrigan - Toby
- Percy Daggs III - Mathlete #2
- Tava Smiley - Carol
- Alexander Gould - Ronnie Johnson
- David Krumholtz - Barry Schweiber
- Ben Stiller - Agent Meara
- Sam McMurray - Dr. Vic Schweiber
- Brianna Brown - The Cheerleader
- Tom Virtue - Mr. Sampson
- Jessica Campbell - Amy Andrews
- Claudia Christian - Gloria Haverchuck
- Kenn Michael - Calvin
- Maura Soden - Mrs. Kent
- Lyle Kanouse - Auto Shop Manager
- Amy Wheaton - Pretty Girl
- Leslie Mann - Miss Foote
- Sarah Hagan - Millie Kentner
- Bianca Kajlich - Piercing Girl
- Trace Beaulieu - Hector Lacovara
- Alan Simpson - Tom
- Rashida Jones - Karen Scarfolli
- Matthew McKane - Mike Stevens
- Matt Czuchry - Teenage Guy #1
- Ann Dowd - Cookie Kelly
- Chauncey Leopardi - Alan White
- Jonathan Kasdan - Tommy
- Jack Conley - Kim Kelly's Stepfather
- Shia LaBeouf - Herbert
- Bill Chott - Señor O'Hara
- Shawnee Free Jones - Jenna Zank
- Riley Smith - Todd Schellinger
- Joel Hodgson - Discotheque DJ
- Ben Foster - Eli
- Gabe Sachs - Drummer
- Olivia Hack - Erin
- Doug Spinuzza - Frank
- Samaire Armstrong - Laurie
- David Koechner - Iron Horse Restaurant Waiter
- Jeff Judah - Sound Mixer
- Samantha Shelton - Heidi Henderson
- Susan Krebs - Housewife
- Thomas F. Wilson - Coach Ben Fredricks
- Alexandra Breckenridge - Shelly Weaver
- Natasha Melnick - Cindy Sanders
- Kayla Ewell - Maureen Sampson
- JoAnna Garcia - Vicki Appleby
- Lizzy Caplan - Sara
- Jason Schwartzman - Howie Gelfand
- Ron Lester - Seidleman
- Lauren Hodges - Mathlete
- Jarrett Lennon - Colin
- Steve Bannos - Frank Kowchevski
- Amy Aquino - Mrs. Schweiber
- Stephanie Erb - Ms. Yeats
- Mark Allan Staubach - Mark
- Stephen Lea Sheppard - Harris Trinsky
- David Doty - Councilman Ritchie
- Steve Higgins - Mr. Fleck
- Meagen Fay - Mrs. Kentner
- John Apicella - Dr. Melvin Latz
- Joel Madison - Mr. Botwinick
- Joanna Canton - Cheerleader
- Laura Bottrell - Beth
- Pamela Gordon - Chain Smoking Woman
- Denalda Williams - Angry Mother
- Renee Cohen - Judith
- Kevin Tighe - Mr. Andopolis
- Jason Lansing - Ernie Hahuth - Bully #1
- Cynthia Windham - Audio Visual Teacher
- Mark Phinney - Drummer #2 (uncredited)
- R.F. Daley - Mr. Mainzer
- David Bowe - Salesman
- Jena Romano - Prissy Girl (uncredited)
- Dave Allen - Jeff Rosso
- Danny Leiner
- Paul Feig
- Judd Apatow
- Ken Kwapis
- Jake Kasdan
- Miguel Arteta
- Patty Lin
- Mike White
- Jeff Judah
- Rebecca Rand Kirshner
- Jonathan Kasdan
- Bob Nickman
- J. Elvis Weinstein
- John Francis Daley
Alexander Gould interpreta a Ronnie Johnson en la serie.
Thomas F. Wilson hace el papel de Coach Ben Fredricks.
John Francis Daley hace el papel de Sam Weir.
Linda Cardellini interpreta a Lindsay Weir en la serie.
James Franco interpreta a Daniel Desario en la serie.
Samm Levine hace el papel de Neal Schweiber.
Martin Starr hace el papel de Bill Haverchuck.
Jason Segel interpreta a Nick Andopolis en la serie.
Seth Rogen interpreta a Ken Miller en la serie.
Joe Flaherty interpreta a Harold Weir en la serie.
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