Rob Helms as Kevin Langstrom

Bruce Daniels as Randall Overbee

Joe Dietl as Royce Cannon

Carrie Aizley as Jocelyn Silverberg

Diane Delano as Sgt. Dot Jenkins

Michael Irpino as Chauncey Ledbetter

Kathy Jensen as Suzy Pleasant

Jennifer Aniston as Clove

Andrea Bendewald as Dust

Tate Donovan as Simon

Nora Dunn as Sandy Delongpre

Taylor Negron as Stewart Sterling

Jeff Rosenthal as Donald Elkins

David Schwimmer as Kelly Goodich / J.T.

Marcus Jacques as Clerk

Bill Escudier as Flower Delivery Guy

Mike Myers as Tim Broderick

Robin Ruzan as Tammy Broderick

Will Ferrell as Darren Clark

Jerry Collins as Tom Phillips

Laura Kightlinger as Amber Jean Rose

Janeane Garofalo as Joyce Wintergarden-Dingle

David Cross as Tommy Dansbury

Vincent Ventresca as Bob

Tuc Watkins as Ted

Emily Whitesell as Betty Sanford

Ben Zook as Faggles / Mr. Wintergarden

Wayzaro Foster as Girl at Party

Margaret Cho as Asia Blue / Terry

Phil LaMarr as Jimmy "Licorice Whip" Wilson

Jimmy Jatho as Skin Head Inmate

Rodney Munoz as Hispanic Inmate

Christine Elise as Darby

Rusty Schwimmer as Nora Finkelheimer

Anne Meara as Mrs. Langstrom

Bob Joles as Mr. Langstrom

Illeana Douglas as Julia Bullock

Mary Lynn Rajskub as Suzy Smokestack

Melanie Hutsell as Yvette Evy

Kevin West as Father Barnes

Megan Cavanagh as Mrs. Ledbetter

Brian Blondell as Mr. Ledbetter

Layne Beamer as Cop

Molly Shannon as Aani

Loretta Fox as Kelly Daneen

Sam Pancake as Randy Nephews

Andy Richter as Ken Irpine

Sarah Thyre as Diane Edbetter-Irpine

Brett Paesel as Karen Hill

Pat Towne as Richard Hill

David Youse as Larry

Joel Murray as Bartender

Tom Booker as Wet Underwear Contestant

Joe Liss as M.C.

Jason Priestley as Hunter Green

Lizzy Murray as Leslie

Promise LaMarco as Script Supervisor

Ingrid Berg as Choreographer

Kate Vogt as Costumer

Jeff Rago as Triple Threat

Kristin Dailey as Swing Choir Member

David Green as Swing Choir Member

Shane Nickerson as Extra #1

Oscar Nunez as Extra #2

Emily Spivey as Extra #3

Bob Dietl as Royce's Father

Jamie Kershaw as Extra #4

Linda Mellano as Extra #5

Kathy Jones as Extra #6

Lisa Galipeau as Craft Service Girl

Terry Sweeney as Make-up Artist

Billy Morrissette as Jack

Maura Tierney as Suzanne

Alexis Arquette as Mr. Ed

Brian McCarthy as Candice Corn

Jon Kean as News Reporter

Scott Williamson as Warden

Eliza Coyle as Angry Protester

Richard Riehle as Governor Eastman

Stephen Wrubel as Mysterious Man in Black

Mike Coleman as Dancing Inmate #1

Rick Grunden as Dancing Inmate #2

Sean Halligan as Dancing Inmate #3

Louis Horvath as Dancing Inmate #4

Eric Hostetter as Wet Underwear Contestant #1

Jerome Roi Maufas as Wet Underwear Contestant #2

Chuck Saculla as Wet Underwear Contestant #3

Stafford Smith as Guard #1

Carl Young as Guard #2

Joey Soloway as Band at Party

Doug Pray as Band at Party

Sam Shneidman as Band at Party

Christian Tasche as Band at Party

John Strozier as Band at Party

Susan Yeagley as Chauncey's New Wife

Christina Izumi as Judy

Victoria Izumi as Cher

Britany Rollerson as Barbra