Directed by Scott Allen Written by Nancy Goodell   Frank Martin   Cast Ron Snow ... Self - Announcer Hugh Hefner ... Self - Editor-In-Chief (as Hugh M. Hefner) Pennelope Jimenez ... Self - Miss March 2003 Marilyn Monroe ... Self (archive footage) Pamela Anderson ... Self - Miss February 1990 Jimmy Kimmel ... Self - TV Host Adam Carolla ... Self - TV Host Drew Carey ... Self - Actor Miriam Gonzalez ... Self - Miss March 2001 Heather Carolin ... Self - Miss April 2002 Kevin Kuster ... Self - Senior Photo Editor Janet Pilgrim ... Self - Miss July 1955 Gary Cole ... Self - Photography Director Arny Freytag ... Self - Senior Contributing Photographer Divini Rae ... Self - Miss November 2003 Dalene Kurtis ... Self - Miss September 2001 Shannon Stewart ... Self - Miss June 2000 Tony Curtis ... Self - Actor Allison Parks ... Self - Miss October 1965 DeDe Lind ... Self - Miss August 1967 Joyce Nizzari ... Self - Miss December 1958 Patti Reynolds ... Self - Miss September 1965 Jo Collins ... Self - Miss December 1964 Liv Lindeland ... Self - Miss January 1971 Marilyn Cole ... Self - Miss January 1972 Patti McGuire ... Self - Playmate of the Year 1977 (archive footage) Marilyn Grabowski ... Self - West Coast Photo Editor Sondra Theodore ... Self - Miss July 1977 (archive footage) Jennifer Jackson ... Self - Miss March 1965 Carmelina Barg ... Self - Miss July 1987 (as Carmen Berg) Stephanie Heinrich ... Self - Miss October 2001 Sharon Osbourne ... Self - Cool Mom Tylyn John ... Self - Miss March 1992 (archive footage) Rebecca Ramos ... Self - Miss January 2003 Angela Melini ... Self - Miss June 1992 (archive footage) Eloise DeJoria ... Self - Miss April 1988 (archive footage) (as Eloise Broady) Carmella DeCesare ... Self - Miss April 2003 Cynthia Myers ... Self - Miss December 1968 Barbara Moore ... Self - Miss December 1992 Kelsey Grammer ... Self - Actor Marketa Janska ... Self - Miss July 2003 Deanna Brooks ... Self - Miss May 1998 Devin DeVasquez ... Self - Miss June 1985 Deborah Driggs ... Self - Miss March 1990 Renee Tenison ... Self - Miss November 1989 Heather Kozar ... Self - Miss January 1998 Shannon Tweed ... Self - Miss November 1981 Debra Jo Fondren ... Self - Miss September 1977 Tina Bockrath ... Self - Miss May 1990 Marcy Hanson ... Self - Miss October 1978 Pompeo Posar ... Self - Playboy Photographer (archive footage) Richard Fegley ... Self - Playboy Photographer (archive footage) Mario Casilli ... Self - Playboy Photographer (archive footage) Dwight Hooker ... Self - Playboy Photographer (archive footage) Stephen Wayda ... Self - Playboy Photographer (archive footage) Martha Smith ... Self - Miss July 1973 Jaclyn Dahm ... Self - Miss December 1998 (as Dahm Triplets) Erica Dahm ... Self - Miss December 1998 (as Dahm Triplets) Nicole Dahm ... Self - Miss December 1998 (as Dahm Triplets) Harry Hamlin ... Self - Actor Candy Loving ... Self - 25th Anniversary Playmate (archive footage) Dorothy Stratten ... Self - 1980 Playmate of the Year (archive footage) Robin Leach ... Self - TV Host Kimberley Conrad ... Self - 1989 Playmate of the Year (archive footage) Lisa Rinna ... Self - Actor Jeff Cohen ... Self - Senior Editor, Special Editions Lisa Dergan ... Self - Miss July 1998 David Hasselhoff ... Self - Actor Keith Hefner ... Self - Hef's Brother Tishara Cousino ... Self - Miss May 1999 Colleen Shannon ... Self - 50th Anniversary Playmate Richard Dawson ... Self (archive footage) Randy Jones ... Self Dick Martin ... Self (archive footage) The Village People ... Themselves (archive footage) Uncredited Cast Claudia Jennings ... Self (archive footage) David LaChapelle ... Self Janice Moses ... Self Christina Santiago ... Self - Miss August 2002 Produced by Ross Dale   Hugh Hefner   Frank Martin   Rudy Poe   Scott Potasnik   Andrew Swift   Michael Trikilis

Additional Info Premiere: September 14, 2004 DVD Release: September 14, 2004 Country: Distributor: Playboy Home Video Websites: Production Companies Playboy Entertainment Group Rating Stats Overall Rating 6.5 / 10 Our Rating -- / 10 Your Friends -- / 10 Male Users -- / 10 Female Users -- / 10 Site Ranking #13,390 / 20,886 Site Ranking #13,384 The Legacy Of Boggy Creek (2011) #13,385 Scarlet Fry's Junkfood Horrorfest (2007) #13,387 Chain Of Souls (2001) #13,388 The Jack In The Box Rises (2024) #13,390 Playboy: 50 Years Of Playmates (2004) #13,391 Cutey Honey Flash: Season 1 (1997) #13,392 Zombie Pirates (2014) #13,393 Goregoyles: The Holy Terror (2003) #13,394 Bite Me If You Love Me (2011)