Lohan's first, and much-talked about cover appearance in Playboy leaked early prior to the publishing of the January/February issue. But Lohan isn't the only star to either begin her career with or at one point end up in Playboy. UPI/Mario Anzuoni/Pool
The list can't be complete without Monroe, who was the covergirl of the very first issue of Playboy in 1953, with a photo of Monroe taken during the 1952 Miss America Parade on the cover, and an older 1949 photo of Monroe serving as the nude shot within the issue. UPI/Brian Kersey
Derek, most famous for her titillating appearances in films during the 1970s and 80s, appeared twice in Playboy during 1980, with a 12-page spread that lead to several further appearances throughout the early 1980s. UPI/Art Foxall.
Anderson may not have been the first to be featured in Playboy, but no one else has modeled for the magazine more times. Since first appearing in the magazine in 1989, Anderson has been on the cover 12 times, and in the magazine itself more than 20 times. UPI/John Angelillo
Initially appearing as Vickie Smith, her birth name, in 1992, Smith was eventually named the 1992 Playmate of the Year and was routinely featured in Playboy, and the tabloids, until her untimely death in 2007. mk/ep/Ezio Petersen UPI
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