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 Don Adams in Playboy After Dark (1969)

Hugh Hefner and Soupy Sales in Playboy After Dark (1969)

Hugh Hefner and Courtney Thorne-Smith in Immer wieder Jim (2001)

Hugh Hefner in Weezer: Beverly Hills (2005)

Hugh Hefner, Holly Madison, Weezer, Rivers Cuomo, Bridget Marquardt, Brian Bell, Kendra Wilkinson, Patrick Wilson, and Scott Shriner in Weezer: Beverly Hills (2005)

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

Hugh Hefner in American Playboy: The Hugh-Hefner-Story (2017)

Carrie Fisher, Penny Marshall, and Hugh Hefner in Laverne & Shirley (1976)

Carrie Fisher and Hugh Hefner in Laverne & Shirley (1976)

Hugh Hefner, Hank Baskett, and Hank Baskett IV in Guess Who's Coming to Calabasas (2012)

Jeffrey Tambor, Hugh Hefner, and Linda Doucett in Die Larry Sanders Show (1992)

Dan Aykroyd and Hugh Hefner in Saturday Night Live (1975)

Eddie Murphy, Jürgen Prochnow, Judge Reinhold, Paul Guilfoyle, Hugh Hefner, and Carrie Leigh in Beverly Hills Cop II (1987)

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

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

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)