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Playboy Magazine, December 1999 [Single Issue Magazine] [Dec 01, 1999] Hugh Hefner

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With 62 years of experience under its risqué belt Playboy is likely to continue producing memorable images, even if they don't include naked women.

Traci Bingham - The first Black actress to don the red swimsuit on Baywatch was featured on the June 1998 cover along with her cast-mate and Playboy staple Pamela Anderson.She was discovered at a football game via a jumbo tron close up, and got this cover on the national magazine two months later. Madonna wasn't one to follow many rules, so it makes perfect sense that she graced Playboy's pages back in her heyday.

Keep in mind that anyone can view public collections - they may also appear in recommendations and other places. There was no interview, and in 2009 the magazine recreated the groundbreaking front page with Marge Simpson.Featuring female government employees posing semi-nude in a 10-page spread, it's obvious how this became one of Playboy's most controversial covers.

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