This large 2-disc/video set is a must-have for Playboy fans with its copious extras, including info sheets and centerfolds on every Playmate of the last fifty years and behind the scenes featurettes on three of the magazine's most noteworthy photographers, Richard Fegley, Arny Freytag and Pompeo Posar. The entire second disc/cassette contains two full-length Playboy features: Playmates of the Year: The '80s and Playmates of the Year: The '90s and a complete Playmate videography organized by girl or by year.

The feature itself is a glossy, hype-heavy promo piece outlining the history of the magazine along with a light focus on the Playmates and their role as cultural icons with a multitude of interviews regarding their Playmate experiences. There's a focus on the "girl next door" image the magazine looks for and brief clips of various mainstream celebrities such as Tony Curtis, Drew Carey, Kelsey Grammer, Sharon Osbourne, Adam Corolla and Jimmy Kimmel talking about how much they love the magazine and the Playboy philosophy that sex is healthy and good.