Hugh Hefner, Holly Madison, Bridget Marquardt, and Kendra Wilkinson in The Girls of the Playboy Mansion (2005)

Hugh Hefner and Holly Madison in The Girls of the Playboy Mansion (2005)

Hugh Hefner and Kendra Wilkinson in The Girls of the Playboy Mansion (2005)

Hugh Hefner, Bridget Marquardt, and Anastasia Case in The Girls of the Playboy Mansion (2005)

Hugh Hefner, Holly Madison, and Bridget Marquardt in The Girls of the Playboy Mansion (2005)

Hugh Hefner and Garry Shandling in Die Larry Sanders Show (1992)

Hugh Hefner in Der Prinz von Bel-Air (1990)

Kim Cattrall and Hugh Hefner in Sex and the City (1998)

Hugh Hefner, Holly Madison, and Kendra Wilkinson in Entourage (2004)

Hugh Hefner, Holly Madison, Bridget Marquardt, and Kendra Wilkinson in House Bunny (2008)

Hugh Hefner, Larry David, and Holly Madison in Lass es, Larry! (2000)

Tony Bennett and Hugh Hefner in Playboy's Penthouse (1959)

Hugh Hefner, Holly Madison, and Kendra Wilkinson in House Bunny (2008)

Hugh Hefner and Nina Simone in Playboy's Penthouse (1959)

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

Hugh Hefner in Secrets of Playboy - Im Bann von Hugh Hefner (2022)

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

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

Anna Nicole Smith and Hugh Hefner in Playboy: 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, 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 Der Prinz von Bel-Air (1990)

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