| Katie Lohmann | ... | Herself | |
| Jaime Bergman | ... | Herself | |
| Renee Tenison | ... | Herself | |
| Kimberley Conrad | ... | Herself (archive footage) | |
| Brandi Brandt | ... | Herself | |
| Candy Loving | ... | Herself (archive footage) | |
| Missy Cleveland | ... | Herself | |
| Rosanne Katon | ... | Herself | |
| Sondra Theodore | ... | Herself (archive footage) | |
| DeDe Lind | ... | Herself | |
| Jennifer Jackson | ... | Herself | |
| Barbi Benton | ... | Herself (archive footage) | |
| Janet Pilgrim | ... | Herself (archive footage) | |
| Hugh M. Hefner | ... | Himself | |
| Christie Hefner | ... | Herself (archive footage) | |
| Phyllis Diller | ... | Herself (archive footage) | |
| Moms Mabley | ... | Herself (archive footage) | |
| Nina Simone | ... | Herself (archive footage) | |
| Tina Turner | ... | Herself (archive footage) | |
| Sarah Vaughan | ... | Herself (archive footage) | |
| Woody Allen | ... | Himself (archive footage) | |
| Louis Armstrong | ... | Himself (archive footage) | |
| Scott Baio | ... | Himself | |
| Count Basie | ... | Himself (archive footage) | |
| Michael Bay | ... | Himself | |
| Tony Bennett | ... | Himself (archive footage) | |
| Milton Berle | ... | Himself (archive footage) | |
| Tom Bradley | ... | Himself (archive footage) | |
| James Brown | ... | Himself (archive footage) | |
| Dave Brubeck | ... | Himself (archive footage) | |
| Lenny Bruce | ... | Himself (archive footage) | |
| James Caan | ... | Himself | |
| George Carlin | ... | Himself (archive footage) | |
| Nat 'King' Cole | ... | Himself (archive footage) | |
| Irwin Corey | ... | Himself (archive footage) (as Professor Irwin Corey) | |
| Bill Cosby | ... | Himself (archive footage) | |
| Tony Curtis | ... | Himself | |
| Vic Damone | ... | Himself | |
| Sammy Davis Jr. | ... | Himself (archive footage) | |
| Richard Dawson | ... | Himself (archive footage) | |
| Dizzy Gillespie | ... | Himself (archive footage) | |
| Seth Green | ... | Himself | |
| Randy Jones | ... | Himself | |
| LeRoy Neiman | ... | Himself | |
| Sidney Poitier | ... | Himself (archive footage) | |
| Tony Randall | ... | Himself (archive footage) | |
| Rex Reed | ... | Himself (archive footage) | |
| Shel Silverstein | ... | Himself (archive footage) | |
| Mel Tormé | ... | Himself (archive footage) | |
| Ike Turner | ... | Himself (archive footage) | |
| Slappy White | ... | Himself (archive footage) | |
| Victor Willis | ... | Himself (archive footage) | |
| Robert Neches | ... | Himself (Announcer) | |
| rest of cast listed alphabetically: | |||
| Christina Smith | |||
Writing credits(in alphabetical order) | ||
| Alicia Good | ||
| Frank Martin | ||
Produced by | |||
| Alicia Good | .... | field producer | |
| Hugh M. Hefner | .... | executive producer | |
| Frank Martin | .... | producer | |
Film Editing by | |||
| Bryan Curb | |||
| Peter Ochs | |||
Production Management | |||
| Jake Deptula | .... | post-production supervisor | |
| Bronston Jones | .... | production manager | |
Costume and Wardrobe Department | |||
| Rebekah Ryan | .... | wardrobe stylist | |
Music Department | |||
| David Forman | .... | music supervisor | |
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| Playboy's 50th Anniversary Celebration | Playboy: Inside the Playboy Mansion | Hugh Hefner: Once Upon a Time | Star 80 | Claudia Jennings |
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| Full cast and crew | Company credits | IMDb Documentary section |
| IMDb USA section |