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Cindy Crawford Playboy Cindy Crawford appeared on the cover of Playboy's July 1988 issue, alongside articles on Jesse Jackson and "The Last Words On Ronald Reagan.

" Playboy has stated that its history of provocative articles and newsmaking interviews will remain intact, even after the makeover -- something the magazine has featured since its very first issue, Hefner explained to CBS' Charlie Rose in 2005.

Hugh Hefner later hinted on his Twitter that the Lohan issue was one of the best-selling in Playboy history.

In a cute play on her television personality, the two Y's in the magazine's name were left out, as if a contestant might soon spin the wheel and shout out that letter.

This 1985 Madonna cover is just one of the most famous.

Insiders said the shoot was designed to be reminiscent of the magazine's inaugural shoot with Marilyn Monroe.

So, when she posed semi-nude for the December 1995 issue of Playboy, it created a bit of a stir.

She appears on numerous covers, in several centerfolds, and even wrote the foreword to the 2012 coffee table book, "Playboy's Greatest Covers.

Not a bad idea considering that web traffic to Playboy's site jumped from about 4 million to 16 million when it removed nudity last year.

Pamela Anderson Playboy Model and actress Pamela Anderson has appeared on more Playboy covers than anyone else.