Anna Nicole Smith and Hugh Hefner in The Complete Anna Nicole Smith (2000)

Hugh Hefner and Brande Roderick in Playboy Exposed: Playboy Mansion Parties Uncensored (2001)

Hugh Hefner in Playboy Exposed: Playboy Mansion Parties Uncensored (2001)

Gwyneth Paltrow, Hugh Hefner, and Brande Roderick in Playboy Exposed: Playboy Mansion Parties Uncensored (2001)

Kevin Spacey and Hugh Hefner in Playboy Exposed: Playboy Mansion Parties Uncensored (2001)

Hugh Hefner, Jeff Altman, Keiko Masuda, and Mie in Pink Lady (1980)

Hugh Hefner, Keiko Masuda, and Mie in Pink Lady (1980)

Hugh Hefner, Crystal Hefner, Holly Madison, Bridget Marquardt, Kendra Wilkinson, Kristina Shannon, and Karissa Shannon in The Girls Next Door (2005)

Hugh Hefner in The Girls Next Door (2005)

Hugh Hefner and Holly Madison in The Girls Next Door (2005)

Hugh Hefner, Holly Madison, Bridget Marquardt, and Kendra Wilkinson in The Girls Next Door (2005)

Hugh Hefner and Kendra Wilkinson in The Girls Next Door (2005)

Hugh Hefner, Bridget Marquardt, and Anastasia Case in The Girls Next Door (2005)

Hugh Hefner, Holly Madison, and Bridget Marquardt in The Girls Next Door (2005)

Hugh Hefner and Judy Carne in Rowan & Martin's Laugh-In (1967)

Jane Curtin, Hugh Hefner, Laraine Newman, and Gilda Radner in Saturday Night Live (1975)

Hugh Hefner, Jeff Altman, Greg Evigan, Keiko Masuda, Mie, Rick Nielsen, Robin Zander, Bun E. Carlos, Tom Petersson, and Cheap Trick in Pink Lady (1980)

Will Smith, Hugh Hefner, Alfonso Ribeiro, and Karyn Parsons in The Fresh Prince of Bel-Air (1990)

Jerry Lewis, Sammy Davis Jr., Hugh Hefner, and Anthony Newley in Playboy After Dark (1969)