In honor of the late Hugh Hefner, who passed away of natural causes at 91 years old at the Playboy Mansion Wednesday (Sept. 27), we rounded up 18 musicians (or musician-adjacents) who have graced the cover of Hefner's legacy that is Playboy Magazine — including Madonna in 1985 (above).
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Madonna
In honor of the late Hugh Hefner, who passed away of natural causes at 91 years old at the Playboy Mansion Wednesday (Sept. 27), we rounded up 18 musicians (or musician-adjacents) who have graced the cover of Hefner's legacy that is Playboy Magazine — including Madonna in 1985 (above).
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Lindsay Lohan
2015
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Dolly Parton
1978
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Ginger Spice
1998
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Kim Kardashian
2007
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Tiffany
2002
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Barbra Streisand
1977
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Paris Hilton
2005
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Mariah Carey
2007
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Nancy Sinatra
1995
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Carmen Electra
2003
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Azealia Banks
2015
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Belinda Carlisle
2001
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LaToya Jackson
1989
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Vanity
1988
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Aubrey O’Day
2009
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Sky Ferreira
2016
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Halsey
2017