Tim Meadows as Leon Phelps

Karyn Parsons as Julie Simmons

Billy Dee Williams as Lester

John Witherspoon as Scrap Iron

Jill Talley as Candy

Lee Evans as Barney

Will Ferrell as Lance DeLune

Sofia Milos as Cheryl

Eugene Levy as Bucky Kent

David Huband as Frank

Ken Hudson Campbell as Hal

Kevin McDonald as Mail Man

Tamala Jones as Theresa

Julianne Moore as Audrey

Tiffani Thiessen as Honey DeLune

Rocky Carroll as Cyrus Cunningham

Arnold Pinnock as V.S.A. Member

Shaun Majumder as V.S.A. Member

Brett Heard as V.S.A. Member

Mark McKinney as Mr. White

Chris Parnell as Phil Swanson

Boyd Banks as C&W Station Manager

Inna Korobkina as Hef's Girl

Reginald Hudlin as Aloysius

April Mullen as Teen Lover

Jammer as Wrestler

Diego Fuentes as V.S.A. Member

Sean Thibodeau as Hugh Hefner

Rebecca Weinberg as Hef's Best Girl

Robyn Palmer as Playboy Bunny

Michelle Silveira as Houseboat Cutie

Simone Stock as Playboy Photographer

Juliet Ladines as Beautiful Girl

Susan Aceron as Chinese lover