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

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The former Playmate, 37, was 21 when she was invited to stay at the Playboy Mansion in October 2008, and a few months later she and the late Playboy mogul entered a relationship – before Crystal became the pornographer’s third wife when they tied the knot in 2012. Anna Nicole Smith, another one of Playboy's major scouts as well as a big-name Playmate of the Year, was on her first cover in 1993. It got annoying, if I am being honest, you are inside and it's an old house the walls are thin, the windows aren't sealed properly, and you would just hear the thump, thump, thump all night long. Appearing in a men's shirt and heels while also holding a glass of alcohol, this cover looks like a whole lot of fun.

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Shari Belafonte - Harry Belafonte's daughter, an actress and singer in her own right, was 46 when she posed for Playboy with the cover line, "Looking Good Naked. For me, it's hard to sleep or go about my business when there is all this stuff happening around me. Jayne Kennedy - Miss Ohio 1970 became the first African-American actress to cover Playboy in July 1981. Inspired by the Darine Stern issue in 1971, Playboy took Marge, the leading lady from the animated TV show The Simpsons, and figured her to pose exactly like Stern — Playboy bunny chair and all.And she has given her honest perspective about her time with Hugh in the mansion in the memoir ‘Only Say Good Things: Surviving Playboy and Finding Myself’. Over the past 62 years in print, the magazine has produced several iconic covers that have certainly set a high bar. Vanity - The "Nasty Girl" singer, aka Prince's "female reflection," took the cover of Playboy's April 1988, six years before she dropped her stage name for evangelism. Hugh Hefner's widow Crystal wasn't allowed to go downstairs to the parties at the Playboy Mansion without him. Etsy’s 100% renewable electricity commitment includes the electricity used by the data centres that host Etsy.