This November 1 1999 issue of Playboy features IBA featherweight champion Mia St John as the cover model and highlights her transition from the boxing ring to a nude pictorial. A central feature of this edition is an extensive interview with Jesse Ventura exploring his potential as the next president and his political views during his tenure as Governor of Minnesota. The magazine also includes the anticipated Sex in Cinema 99 pictorial which reviews the year in film along with an exclusive preview of the Dune science fiction prequel.

Readers will find additional content such as new fiction by Scott Turow a feature on country legend George Jones and a report on college campus life. With Canadian model Cara Wakelin as the Playmate of the Month this issue remains a significant piece of late nineties pop culture for collectors of lifestyle media and sports history.

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