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Year 1999 Archive — Digital PDF Downloads Available Now

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1953 … 1992 1993 1994 1995 1996 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 … 2025
Playboy Jan 1999
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Playboy January 1999
Features
Covergirl Marilyn Monroe Composite Image (Nude) photographed by Rob Silvers
Playmate of the Month is Jaime Bergman photographed by Stephen Wayda
Sex Stars Of The Century
Playboy Interview: Michael Crichton
Playboy Feb 1999
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Playboy February 1999
Features
Covergirl Pamela Anderson (Nude) photographed by Stephen Wayda
Playmate of the Month is Stacy Fuson photographed by Arny Freytag
The Naked and the Dead by A.J. Benza
NFL Cheerleaders Nude
Playboy Mar 1999
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Playboy March 1999
Features
Covergirl Kiss Girls (Nude) photographed by Arny Freytag
Playmate of the Month is Alexandria Karlsen
The Girls Of Kiss
Will Your Relationship Last? by Craig Vetter
Playboy Apr 1999
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Playboy April 1999
Features
Covergirl Sable (Nude) photographed by Arny Freytag
Playmate of the Month is Natalia Sokolova photographed by Stephen Wayda and Arny Freytag
Spring Break: The Girls, The Beaches, The Bars, The Thongs
WWF Sex Sensation Sable Nude
Playboy May 1999
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Playboy May 1999
Features
Covergirl Charlize Theron (Nude) photographed by Guido Argentini
Playmate of the Month is Tishara Lee Cousino photographed by Arny Freytag
Playboy Interviews David Spade
Mighty Charlize Theron Nude
Playboy Jun 1999
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Playboy June 1999
Features
Covergirl Heather Kozar (Nude) photographed by Arny Freytag
Playmate of the Month is Kimberly Spicer photographed by Richard Fegley
The 20th Century's Ultimate Playmate Of The Year: Heather Kozar, 16 Great Pages
Let's Get In to Character: Playboy Interviews Samuel L. Jackson
Playboy Jul 1999
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Playboy July 1999
Features
Covergirl Brooke Richards (Nude) photographed by Arny Freytag
Playmate of the Month is Jennifer Rovero photographed by Arny Freytag and Stephen Wayda
The Girls Of Hawaiian Tropic
Wrestling Madness: The Stars, The Brawls, The Girl
Playboy Aug 1999
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Playboy August 1999
Features
Covergirl Nell McAndrew (Nude) photographed by Richard McLaren
Playmate of the Month is Rebecca Scott photographed by Stephen Wayda
Tomb Raider: Nell McAndrew, A.K.A. Lara Croft, Nude
A Funny, Funny Interview With Albert Brooks
Playboy Sep 1999
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Playboy September 1999
Features
Covergirl Sable (Nude) photographed by Arny Freytag
Playmate of the Month is Kristi Cline photographed by Stephen Wayda
E-Crime: Don't Get Mugged in Cyberspace
Sable II: The Rematch, 14 Great All-New Pages
Playboy Oct 1999
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Playboy October 1999
Features
Covergirl Jennifer Rovero (Nude) photographed by Arny Freytag
Playmate of the Month is Jodi Ann Paterson photographed by Arny Freytag
Girls Of The PAC 10
Jazz & Rock Poll
Playboy Nov 1999
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Playboy November 1999
Features
Covergirl Mia St. John (Nude) photographed by Arny Freytag
Playmate of the Month is Cara Wakelin photographed by Richard Fegley
Sex In Cinema '99
The Next President? Jesse "The Interview" Ventura
Playboy Nov 1999
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Playboy November 1999, Canadian Cover
Features
Covergirl & Playmate of the Month Cara Wakelin (Nude & Centerfold) photographed by James Imbrogno
Sex In Cinema '99
The Next President? Jesse "The Interview" Ventura
I.B.A. Featherweight Champion Mia St. John Nude
Playboy Dec 1999
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Playboy December 1999
Features
Covergirl Naomi Campbell (Nude) photographed by David LaChapelle
Playmate of the Month is Brooke Richards photographed by Stephen Wayda
Holiday Contributors: Wynton Marsalis, Donald Westlake, Leroy Neiman & More
Naomi Campbell Incredibly Nude
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