Cast
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Mark Chinnery
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Hugh Hefner
(10 episodes)
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Hugh Hefner
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Self
(7 episodes)
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Andrew Cereghino
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Stefan Tettenbaum
(4 episodes)
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Sondra Theodore
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Self - Hefner's Girlfriend, 1976-1981
(3 episodes)
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Richard W. Bann
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Self - Hefner's Friend
(2 episodes)
(as Richard Bann)
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Joel Berliner
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Self - Hefner's Friend
(2 episodes)
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Miki Garcia
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Self - Playmate & Head of Promotions, 1973-1982
(2 episodes)
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Chris Jones
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Self - Journalist
(2 episodes)
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Leon Isaac Kennedy
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Self - Hefner's Friend
(2 episodes)
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Jamilah Lemieux
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Self - Cultural Critic
(2 episodes)
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P.J. Masten
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Self - LA & Chicago Bunny Mother, 1972-1982
(2 episodes)
(as PJ Masten)
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Jaki Nett
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Self - Los Angeles Bunny Trainer, 1967-1979
(2 episodes)
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Jennifer Saginor
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Self - Author, Playground: A Childhood Lost Inside the Playboy Mansion
(2 episodes)
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Stella Tetenbaum
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Self
(2 episodes)
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Johnny Keatth
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Dr. Mark Saginor
(2 episodes)
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Alysse Fozmark
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Miki Garcia
(2 episodes)
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Dona Speir
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Self
(2 episodes)
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Lisa Guerrero
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Self - Host
(2 episodes)
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Susan Brownmiller
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Self - Feminist Activist
(archive footage)
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Sammy Davis Jr.
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Self
(archive footage)
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Reilly Jacquemin
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Young Jennifer Saginor
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Pat O'Brien
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Self - West Coast Correspondent
(archive footage)
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Lisa Page
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Self - Playboy Editorial Assistant, 1984-1985
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Mitch Rosen
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Self - Butler, 1983-1989
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Bogdan Szumilas
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H. Hefner Butler
(as Tim Davis)
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Stefan Tetenbaum
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Self - Hefner's Valet, 1978-1981
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Pamela Anderson
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Self
(archive footage)
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Jonathan Baker
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Self - Hefner's Friend
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Alexandra Cooper
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Self - Host, 'Call Her Daddy' Podcast
(archive footage)
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Carla Howe
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Self - Playboy Model
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Larry King
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Self
(archive footage)
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Sharmagne Leland-St. John
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Self - Playboy Photographer
(as Sharmagne Leland-St.John-Sylbert)
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Charlotte Lewis
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Self - Playboy Cover Model
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Katie Lohmann
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Self - Playmate & Hefner's Girlfriend, 2001
(archive footage)
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Holly Madison
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Self - Hefner's Girlfriend, 2001-2008
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Bridget Marquardt
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Self - Hefner's Girlfriend, 2002-2008
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Jenny McCarthy-Wahlberg
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Self
(archive footage)
(as Jenny McCarthy Wahlberg)
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Alison Reynolds
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Self - Hefner's Friend and Photographer
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Anna Nicole Smith
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Self
(archive footage)
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Anuschka van Lent
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Throwback of Holy Madison
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Suzanne Charneski
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Self - Great Gorge Bunny, 1979-1982
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Rachel Deutsch
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Valerie Cragin
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Jim Ellis
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Self - Hefner's Bodyguard, 1980-1981
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Gayla Guenot
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Self - Los Angeles Bunny, 1978-1986
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Keith Hefner
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Self - Hugh Hefner's Brother & Playboy Executive
(archive footage)
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Russell Miller
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Self - Author, Bunny
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Susanne Singer
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Self - Century City Bunny, 1972-1984
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Sophie Jordan Collins
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Young Susie Krabacher
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Rebekka Armstrong
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Self
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Cristy Thom
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Self
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Erryn Leigh
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Young PJ Masten
(credit only)
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Karissa Shannon
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Self
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Kristina Shannon
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Self
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Lisa Loving Barrett
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Self
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