Hugh Hefner (10 episodes, 2017)
Victor Lownes (10 episodes, 2017)
A.C. Spectorsky (10 episodes, 2017)
Bobbie Arnstein (10 episodes, 2017)
Art Paul (10 episodes, 2017)
Arthur Kretchmer / Arthur Kretchner (10 episodes, 2017)
Bob Preuss (10 episodes, 2017)
James Thompson (10 episodes, 2017)
Paul Snider (10 episodes, 2017)
James McGinn (10 episodes, 2017)
Janet Pilgrim / Charlaine Karalus (10 episodes, 2017)
John Baumgarth (10 episodes, 2017)
Gaming Commissioner (10 episodes, 2017)
William R. Ming Jr. (10 episodes, 2017)
Cynthia Maddox (10 episodes, 2017)
Dorothy Stratten / Dorothy Stratton (10 episodes, 2017)
Judge Decker (10 episodes, 2017)
Judge Matkovic (10 episodes, 2017)
Derick Daniels (10 episodes, 2017)
Dr. David Busby (10 episodes, 2017)
Millie Hefner (10 episodes, 2017)
Barbi Benton (10 episodes, 2017)
Time Magazine Interviewer (10 episodes, 2017)
George Matthews (10 episodes, 2017)
Gloria Steinem (10 episodes, 2017)
Mr. Taylor (10 episodes, 2017)
John Melaniphy (10 episodes, 2017)
Hefner's Date (10 episodes, 2017)
Ron Scharf (10 episodes, 2017)
Marilyn Cole (10 episodes, 2017)
Hef's Lawyer (10 episodes, 2017)
Christie Hefner (10 episodes, 2017)
Time Magazine Photographer (10 episodes, 2017)
TV Producer #1 (10 episodes, 2017)
Dick Rosenzweig (9 episodes, 2017)
Vince Tajiri (9 episodes, 2017)
Arnie Morton (9 episodes, 2017)
Self (7 episodes, 2017)
Ray Russell (6 episodes, 2017)
Eldon Sellers (6 episodes, 2017)
Jessica (2 episodes, 2017)
Counsellor Summerfield (2 episodes, 2017)
Teddy Howard (2 episodes, 2017)
Self (2 episodes, 2017)
Reporter (1 episode, 2017)
Self (1 episode, 2017)
Malcolm X (1 episode, 2017)
Teen Hugh Hefner (1 episode, 2017)
Nurse Claire (1 episode, 2017)
Self (uncredited) (1 episode, 2017)