This May 1999 edition of the iconic men’s entertainment magazine features a captivating cover appearance by Charlize Theron at the height of her cinematic rise.

The issue offers a quintessential late nineties cultural snapshot with a lineup including a revealing interview with David Spade and 20 Questions with Ashley Judd. Readers can explore diverse editorial content ranging from a unique romantic profile of Ben Stiller and Janeane Garofalo to Molly Ivins reporting on Tom DeLay. Highlighting the global and seasonal interests of the era the pages include a feature on Moscow titled In the Raw along with a comprehensive 1999 baseball preview and a themed pictorial of playmates on safari.

This publication remains a significant piece of media history for collectors interested in the intersection of Hollywood celebrity and long form journalism during the turn of the millennium.