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Anderson's first Playboy cover below came after starring in a series of beer commercials.

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The 25 most famous women to appear on Playboy's cover

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Her American cover shot in coincided with her marriage to Sean Penn and her appearance in "Desperately Seeking Susan.

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Description: But she didn't appear in it the most. She signed her first international cosmetics contract with Cosmopolitan Cosmetics the same year she was the American cover model, according to Vogue.

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