The September 1999 issue of Playboy stands as a premier artifact of late nineties pop culture featuring the highly anticipated return of wrestling superstar Sable in a pictorial titled The Rematch. This edition highlights the era through a bold and bad interview with comedian Chris Rock and a 20Q feature with Jeri Ryan of Star Trek fame.

Alongside fourteen all new pages of exclusive photography the magazine explores contemporary concerns like E-Crime in cyberspace while providing a Pro Football Forecast and a Playboy Preview 2000. As a significant release for both sports entertainment enthusiasts and collectors of iconic celebrity media this volume represents a peak moment in the publication's history.