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Directed by: | Edith Becker | Written by: | Edith Becker andKevin Burns | Released: | February 10, 2002 | Cast: | Rino Romano as. Narrator (voice)
| | rest of cast listed alphabetically
| | Pamela Anderson as. Herself
| Richard Bann as. Interviewee: Film Historian
| Barbi Benton as. Interviewee: Former Girlfriend
| | | Michael Caine as. Himself (archive footage)
| | | Jim Carrey as. Himself
| Kimberley Conrad as. Interviewee: Wife/Playmate of the Year 1989
| | | | | Leonardo DiCaprio as. Himself
| | Alice Faye as. Herself (archive footage)
| | Sarah Michelle Gellar as. Herself
| Dick Gregory as. Interviewee: Comedian/Activist
| | Cooper Hefner as. Himself
| | Hugh M. Hefner as. Himself
| Keith Hefner as. Interviewee: Brother
| | Marston Hefner as. Himself
| | Randy Jones as. Himself/Village People
| Tina Jordan as. Interviewee: Girlfriend/Playmate
| | Allan Kent as. Himself
| | Peter Lawford as. Himself (archive footage)
| Katie Lohmann as. Interviewee: Girlfriend/Playmate
| Bill Maher as. Interviewee: Comedian/Talk Show Host
| | LeRoy Neiman as. Interviewee: Artist
| Joyce Nizzari as. Interviewee: Former Girlfriend/Playmate
| Mary O’Connor as. Interviewee: Personal Secretary to Hugh Hefner
| Camille Paglia as. Interviewee: Educator/Author
| | Sarah Jessica Parker as. Herself
| | Jodi Ann Paterson as. Herself
| David Robinson as. Staff: Playboy Mansion West
| | Brande Roderick as. Herself
| Mark Saginor as. Interviewee: Hugh Hefner’s Physician (as Mark Saginor, M.D.)
| Mort Sahl as. Interviewee: Comedian
| | Kevin Spacey as. Himself
| | Ben Stiller as. Himself
| Christina Hoff Summers as. Interviewee: Educator/Author
| Joy Tarbell as. Interviewee: Former Playboy Bunny
| | Shannon Tweed as. Herself
| Buffy Tyler as. Interviewee: Girlfriend/Playmate
| | Bill Zehme as. Interviewee: Journalist
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