Playboy: Playmate Pajama Party (1999)

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. Title switches between filmed segments and sequences shot on video (believed to be a first for Playboy).