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Playboy Magazine

Playboy founder Hugh Hefner passed away this week at age 91. As the world grapples with his legacy, here's a look back at some of the most famous stars who have graced his magazine's cover over the years.

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Playboy Magazine
Marilyn Monroe

December 1953

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Jayne Mansfield

June 1963

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Raquel Welch

December 1979

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Steve Martin

January 1980

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Bo Derek

March 1980

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Kim Basinger

February 1983

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Joan Collins

December 1983

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Goldie Hawn

January 1985

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Madonna

September 1985

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Brooke Shields

December 1986

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Vanna White

May 1987

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Cindy Crawford

July 1988

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La Toya Jackson

March 1989

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Sharon Stone

July 1990

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Sherilyn Fenn

December 1990

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Shannen Doherty

March 1994

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Elle Macpherson

May 1994

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Pamela Anderson

November 1994

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Drew Barrymore

January 1995

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Farrah Fawcett

December 1995

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Geri Halliwell

May 1998

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Lisa Rinna

September 1998

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Charlize Theron

May 1999

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Kristy Swanson

November 2002

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Dita Von Teese

December 2002

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Tia Carrere

January 2003

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Daryl Hannah

November 2003

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Jaime Pressly

February 2004

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Rachel Hunter

April 2004

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Charisma Carpenter

June 2004

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