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Browse all of the Maxim Magazine covers from 1999. See the sexiest women of 1999 on the covers of Maxim.

Bridget Fonda January/February 1999, Issue 15

Rose McGowan March 1999, Issue 16 -

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Lucy Lawless April 1999, Issue 17 -

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Caprice May 1999, Issue 18 -

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Shannen Doherty June 1999, Issue 19 -

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Michelle Williams July/August 1999, Issue 20 -

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Pamela Anderson September 1999, Issue 21 -

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Melissa Joan Hart October 1999, Issue 22

Jennifer Love Hewitt November 1999, Issue 23 -

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Lara Flynn Boyle December 1999, Issue 24 -

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Maxim Cover Girls 1999 | Maxim Magazine Covers Gallery