| Name | Character | Episodes |
|---|---|---|
| Holly Madison | Self - Former Playmate | 13 |
| Hugh Hefner | Self (archive footage) | 8 |
| Holly Madison | 6 | |
| Jeana Keough | Self - Playmate of the Month, November 1980 | 2 |
| Mia Farrow | Self - Rosemary (archive footage) | 1 |
| John Travolta | Self (archive footage) | 1 |
| Ben Stiller | Self (archive footage) | 1 |
| Gene Hackman | Self (archive footage) | 1 |
| Christine Taylor | Self (archive footage) | 1 |
| Conan O'Brien | Self (archive footage) | 1 |
| Dorothy Stratten | Self (archive footage) | 1 |
| Roman Polanski | Self (archive footage) | 1 |
| Jon Stewart | Self (archive footage) | 1 |
| Brande Roderick | Self (archive footage) | 1 |
| Victoria Vetri | Self (archive footage) | 1 |
| Bridget Marquardt | Self (archive footage) | 1 |
| Bridget Marquardt | Self - Former Playboy Model | 1 |
| Johnny Carson | Self (archive footage) | 1 |
| Sharon Tate | Self (archive footage) | 1 |
| Dre Davis | Paula Sladewski | 1 |
| Colleen Shannon | Self - Former Playmate | 1 |
| Amber Campisi | Self - Former Playmate | 1 |