| Person | Type | Job | Role(s) | Episodes |
|---|---|---|---|---|
 Ben Stiller | Cast | Actor | Self (archive footage) | 1 |
 Brande Roderick | Cast | Actress | Self (archive footage) | 1 |
 Christine Taylor | Cast | Actress | Self (archive footage) | 1 |
 Conan O'Brien | Cast | Actor | Self (archive footage) | 1 |
 Dorothy Stratten | Cast | Actress | Self (archive footage) | 1 |
 Gene Hackman | Cast | Actor | Self (archive footage) | 1 |
 Holly Madison | Cast | Actress | Self - Former Playmate | 13 |
 Hugh Hefner | Cast | Actor | Self (archive footage) | 8 |
 Jeana Keough | Cast | Actress | Self - Playmate of the Month, November 1980 | 2 |
 John Travolta | Cast | Actor | Self (archive footage) | 1 |
 Johnny Carson | Cast | Actor | Self (archive footage) | 1 |
 Jon Stewart | Cast | Actor | Self (archive footage) | 1 |
 Mia Farrow | Cast | Actress | Self - Rosemary (archive footage) | 1 |
 Roman Polanski | Cast | Actor | Self (archive footage) | 1 |
 Sharon Tate | Cast | Actress | Self (archive footage) | 1 |
 Victoria Vetri | Cast | Actress | Self (archive footage) | 1 |
 Amber Campisi | Cast | Actress | Self - Former Playmate | 1 |
 Bridget Marquardt | Cast | Actress | Self - Former Playboy Model | 1 |
 Colleen Shannon | Cast | Actress | Self - Former Playmate | 1 |
 Kendra Wilkinson | Cast | Actress | Self (archive footage) | 2 |
 Tia Barr | Cast | Actress | Mandy Bentley | 1 |
 Dre Davis | Cast | Actress | Paula Sladewski | 1 |
 Talon Reid | Cast | Actor | Self - Kelsey's friend | 1 |
 Bobby Liga | Cast | Actor | Jon Logan | 1 |
 Sarah Moliski | Cast | Actress | Star Stowe | 1 |
 Emily Pokora | Cast | Jasmine Fiore | 1 | |
Jordan Bell | Cast | Actor | 1 | |
Joseph DiMartino | Cast | Actor | Black Bart/ Chuck Gold | 6 |
| Person | Type | Job | Role(s) | Episodes |
