Ryan Reynolds as Van Wilder

Tara Reid as Gwen Pearson

Tim Matheson as Vance Wilder Sr.

Kal Penn as Taj Mahal Badalandabad

Teck Holmes as Hutch

Daniel Cosgrove as Richard Bagg

Deon Richmond as Mini Cochran

Alex Burns as Gordon

Emily Rutherfurd as Jeannie

Paul Gleason as Professor McDoogle

Erik Estrada as Erik Estrada

Curtis Armstrong as Campus Cop

Jason Winer as Panos Patakos

Chris Owen as Suicidal Freshman

Simon Helberg as Vernon

Aaron Paul as Wasted Guy

Ivana Bozilovic as Naomi

Kim Smith as Casey

Teresa Hill as Hot Female Doctor

Megan Gallagher as Holyoke Hottie

Jason Hopkins as Sick Boy

Lydia Hull as Lindsey

Mark Chaet as Business Manager

Michael Waltman as Coach Ken Massey

Cynthia Fancher as Ms. Haver

Michael Olowokandi as Leron

Darius Miles as Darius

Quentin Richardson as Quentin

Lamar Odom as Coolidge Chickadee Player

Nick Puga as Pimply Faced Freshman

Joshua Swanson as Annoyingly Peppy Freshman

Jesse Capelli as Desiree

Ronald Hunter as Gus

Jeremy Phillips as Overweight Freshman

Darcy Shean as Gwen's Mom

Harry Danner as Dr. Beeverman

Tom Howard as Gwen's Dad

John Colton as Dr. Henke

Sophia Bush as Sally

J. Patrick McCormack as Dean Mooney

Gregg Daniel as English Professor

Lauren Birkell as Cheesy TV Announcer

Teesha Lobo as Hot Indian Girl

Cheryl Bricker as Mrs. Henke

Christopher Sowers as Thin Pledge

Colin Campbell as Archive Guy

Willie Latimore as Ming Impersonator

Sean Marquette as Little Kid

Sterling Rice as Little Girl

Albert Owens as Another Doctor

Anderson Goncalves as Dorky Brother

Anne Varnishung as Gorgeous Secretary

Erik Audé as Martial Arts Freshman

Sarah Fairfax as Mrs. Seay

Travis McKenna as Milty

Lou Beatty Jr. as Library Man

Andrew Bilgore as Party Busting Cop

Alexia Chiaromonte as Stunning Co-Ed Freshman

Brent Goldberg as Freshman Interviewee 1

David Wagner as Freshman Interviewee 2

Chad Evans as Stoner Freshman

Brandon Kessel as College Kid

Ryan Carlberg as Worried Preppy Freshman

Matt Newton as Male Sophomore

Edie McClurg as Campus Tour Guide

Joyce Brothers as Dr. Joyce Brothers

Shaina Fewell as Hot Senior

Megan Litwin as Hotter Friend

Sarah Paul as Terri

Michelle Thomas as Sherri

Sirin Suprasert as Suk Mee

Mark Alfa as Tranny Stripper (uncredited)

Megan Baker as Student (uncredited)

Walt Becker as Fireman (uncredited)

Jason Berry as Frat Boy (uncredited)

Sean Brennan as Shoeshine DIK (uncredited)

Chad Brokaw as DIK Brother (uncredited)

Ryan Allen Carrillo as Roller Skater (uncredited)

Heather Charles as Luau Girl (uncredited)

Tom Everett Scott as Elliot Grebb (uncredited)

Soren Fulton as 10-Year-Old Boy (uncredited)

Reid Godshaw as Drunk Boy (uncredited)

Sean Gordon as Roller Skater (uncredited)

Christopher D. Grace as Drunken Frat Guy (uncredited)

Kelly Hayes as Luau Party Guy (uncredited)

Jesse Heiman as Student on Couch (uncredited)

Summer Moore as Pajama Party Goer (uncredited)

Bonnie Morgan as Twisted Auditioner (uncredited)

Alex Nesic as ROTC Student (uncredited)

Steffen Schlachtenhaufen as Student Bartender (uncredited)

Jennifer Schlueter as Student (uncredited)

Skyler Stone as Test Taker (uncredited)

Charlie Talbert as Stomach Guy (uncredited)

Billy Taylor as Student (uncredited)

Nathan Todaro as Skating Rink Geek (uncredited)

Cassie Townsend as Student (uncredited)

Greta Valenti as Hot Roller Girl (uncredited)

Josh Waters as College Student on Campus Tour (uncredited)

Nik Wilcox as Sycophant (uncredited)