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Lindsay Lohan

"New York," 2008; "Playboy," 2012 2002

After a few revealing paparazzi shots surfaced, there wasn't much of Lindsay Lohan the public hadn't seen by 2008. But the starlet did nudity on her own terms for "New York" magazine's "Spring Fashion" issue, when she covered up with only a sheer scarf in homage to Marilyn Monroe's final photo shoot. Four years (and several court appearances) later, LiLo attempted to launch a comeback by undressing for another Monroe-inspired nude shoot. This time she posed for "Playboy," and according to a tweet from Hugh Hefner, her issue broke sales records for the magazine.

(CREDIT: Courtesy of New York/Playboy)
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