Every Playmate in Playboy's 50-Year history all in one collectors edition.
| Actor | Role |
|---|---|
 Hugh HefnerSelf - Editor-In-Chief | Self - Editor-In-Chief |
 Pamela AndersonSelf - Miss February 1990 | Self - Miss February 1990 |
 Marilyn MonroeSelf (archive footage) | Self (archive footage) |
 Shannon StewartSelf - Miss June 2000 | Self - Miss June 2000 |
 Carmella GarciaSelf - Miss April 2003 | Self - Miss April 2003 |
 Dorothy StrattenNot listed | Not listed |
 Claudia JenningsNot listed | Not listed |
 Sondra TheodoreNot listed | Not listed |
 Cynthia MyersNot listed | Not listed |
 Kimberley ConradNot listed | Not listed |
 Eloise DeJoriaNot listed | Not listed |
 Barbara MooreNot listed | Not listed |
 Colleen ShannonNot listed | Not listed |
 Deborah DriggsNot listed | Not listed |
 Jaclyn DahmNot listed | Not listed |
 Diane Gayle LindSelf | Self |