A departure from the traditional Playboy video fare. Title is shot entirely on the grounds of the Playboy Mansion, and includes some historic footage regarding the events that took place there. The Playmates explore the grounds, including: swimming in and sunning themselves beside the Grotto; roaming au naturel through Hef's private menagerie; playing a clothing-challenged game of tennis; relaxing with a full-body-massage and a hot shower; playing an impromptu game of strip poker; shooting pool, and celebrating good shots by disrobing; taking a nighttime dip in the Grotto; and engaging in a pillow fight, where the first casualties are their tiny outfits.
| Actor | Role |
|---|---|
 Tori SpellingNot listed | Not listed |
 Shannen DohertyNot listed | Not listed |
 Stacy SanchesNot listed | Not listed |
 Alexandria KarlsenNot listed | Not listed |
 Vanessa GleasonNot listed | Not listed |
 Stacy FusonNot listed | Not listed |
 Jaime BergmanNot listed | Not listed |
 Jennifer Lynn AllanNot listed | Not listed |
 Elisa BridgesNot listed | Not listed |
 Laura CoverNot listed | Not listed |
 Deanna BrooksNot listed | Not listed |
 Lisa DerganNot listed | Not listed |
 Layla RobertsNot listed | Not listed |
 Heather KozarNot listed | Not listed |
 Victoria SilvstedtNot listed | Not listed |
 Ava FabianNot listed | Not listed |
 Denise KelloggNot listed | Not listed |
 Sondra TheodoreNot listed | Not listed |
 Roberta VasquezNot listed | Not listed |
 Shannon TweedNot listed | Not listed |
 Laura LyonsNot listed | Not listed |
 Susan KigerNot listed | Not listed |
| HHope OlsonNot listed | Not listed |
| LLisa SohmNot listed | Not listed |
 Hugh HefnerNot listed | Not listed |
 Jim CarreyNot listed | Not listed |
 George ClooneyNot listed | Not listed |
 Bill CosbyNot listed | Not listed |
 Jack NicholsonNot listed | Not listed |
 James CaanNot listed | Not listed |