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1
Marilyn Monroe (Dec. 1953)
She was the first—a classic cover.
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2
Naomi Campbell (Dec. 1999)
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3
Anna Nicole Smith (Feb. 1994)
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4
Drew Barrymore (Jan. 1995)
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5
Marge Simpson (Nov. 2009)
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6
Pamela Anderson (July 1992)
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7
Kim Kardashian (Dec. 2007)
No champagne here.
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8
Dolly Parton (Oct. 1978)
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9
Carmen Electra (April 2003)
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10
Farrah Fawcett (Dec. 1978)
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11
Diane Stern (Oct. 1971)
The first African-American on the cover of Playboy.
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12
Aubrey O'Day (March 2009)
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13
Cindy Crawford (Oct. 1998)
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14
Tara Reid (Jan/Feb 2010)
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15
Donald Trump (March 1990)
Luckily for everyone, he kept his clothes on.
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