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45th Anniversary Issue
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Playboy January 1999
Playboy's Playmate of the Month
Jamie Bergman photographed by Stephen Wayda Covergirl
Marilyn Monroe Composite Image (Nude inside) photographed by Rob Silvers Interview
Michael Crichton by Playboy
Features
Sex Stars Of The Century
Playboy Interview: Michael Crichton
Last Words For A Century
Earth To Universe: Do You Read?
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Playboy February 1999
Playboy's Playmate of the Month
Stacy Fuson photographed by Arny Freytag Covergirl
Pamela Anderson (Nude inside) photographed by Stephen Wayda Interview
Emeril Lagasse by Playboy
Features
The Naked and the Dead by A.J. Benza
NFL Cheerleaders Nude
The End Is Near And Pat Robertson Is Ecstatic
Adam Sandler Q&A: Dumb Questions, Dumb Answers
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Sex & Music Issue
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Playboy March 1999
Playboy's Playmate of the Month
Alexandria Karlsen photographed by Stephen Wayda and Arny Freytag Covergirl
Kiss Girls (Nude inside) photographed by Arny Freytag Interview
Drew Carey by Playboy
Features
The Girls Of Kiss
Will Your Relationship Last? by Craig Vetter
Exclusive Fiction Preview: The Return Of Little Big Man
Seductive Rudolph Giuliani, Irresistible Keith Olbermann
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Playboy April 1999
Playboy's Playmate of the Month
Natalia Sokolova photographed by Stephen Wayda and Arny Freytag Covergirl
Sable (Nude inside) photographed by Arny Freytag Interview
Nick Nolte by Playboy
Features
Spring Break: The Girls, The Beaches, The Bars, The Thongs
WWF Sex Sensation Sable Nude
Web cams, is the sex live or jive?
20 questions: David Schwimmer
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Playboy May 1999
Playboy's Playmate of the Month
Tishara Lee Cousino photographed by Arny Freytag Covergirl
Charlize Theron (Nude inside) photographed by Guido Argentini Interview
David Space by Playboy
Features
Playboy Interviews David Spade
Mighty Charlize Theron Nude
Talk About Nature's Wonders: Playmates On Safari
Ben Stiller and Janeane Garofalo: A Strange Romance Revealed
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Playboy June 1999
Playboy's Playmate of the Month
Kimberly Spicer photographed by Richard Fegley Covergirl
Heather Kozar (Nude inside) photographed by Arny Freytag Interview
Samuel L. Jackson by Playboy
Features
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
What's After Viagra? A Special Report
Star Wars: The guns, The Babes, The Preview
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Playboy July 1999
Playboy's Playmate of the Month
Jennifer Rovero photographed by Arny Freytag and Stephen Wayda Covergirl
Brooke Richards (Nude inside) photographed by Arny Freytag Interview
Barney Frank by Playboy
Features
The Girls Of Hawaiian Tropic
Wrestling Madness: The Stars, The Brawls, The Girl
Gay, Jewish, Left-Handed, Outspoken Congressman Barney Frank Interviewed
Bill Maher's Chocolate Fantasies
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Playboy August 1999
Playboy's Playmate of the Month
Rebecca Scott photographed by Stephen Wayda Covergirl
Nell McAndrew (Nude inside) photographed by Richard McLaren Interview
Albert Brooks by Playboy
Features
Tomb Raider: Nell McAndrew, A.K.A. Lara Croft, Nude
A Funny, Funny Interview With Albert Brooks
American Pie's Shannon Elizabeth: Hot New Sex Star
Playboy's Wizard Broker Says, "Make More Money Now"
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Playboy September 1999
Playboy's Playmate of the Month
Kristi Cline photographed by Stephen Wayda Covergirl
Sable (Nude inside) photographed by Arny Freytag Interview
Chris Rock by Playboy
Features
E-Crime: Don't Get Mugged in Cyberspace
Sable II: The Rematch, 14 Great All-New Pages
20Q Star Trek's Luscious Jeri Ryan
Playboy's Preview 2000
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Cool College Issue
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Playboy October 1999
Playboy's Playmate of the Month
Jodi Ann Paterson photographed by Arny Freytag Covergirl
Jennifer Rovero (Nude inside) photographed by Arny Freytag Interview
Kevin Spacey by Playboy
Features
Girls Of The PAC 10
Jazz & Rock Poll
1st Among Forecasters, Playboy's Pigskin Preview
20Q: Baseball Class Act Joe Morgan
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Playboy November 1999
Playboy's Playmate of the Month
Cara Wakelin photographed by Richard Fegley Covergirl
Mia St. john (Nude inside) photographed by Arny Freytag Interview
Jesse Ventura by Playboy
Features
Sex In Cinema '99
The Next President? Jesse "The Interview" Ventura
I.B.A. Featherweight Champion Mia St. John Nude
History Of The Sexual Revolution: The Final Chapter
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Playboy November 1999 - Canadian Cover
Playboy's Playmate of the Month
Cara Wakelin (covergirl) photographed by Richard Fegley Covergirl
Cara Wakelin (Nude inside and also appears as the centerfold) photographed by James Imbrogno Interview
Jesse Ventura by Playboy
Features
Sex In Cinema '99
The Next President? Jesse "The Interview" Ventura
I.B.A. Featherweight Champion Mia St. John Nude
History Of The Sexual Revolution: The Final Chapter
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Gala Christmas Issue
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Playboy December 1999
Playboy's Playmate of the Month
Brooke Richards photographed by Stephen Wayda Covergirl
Naomi Campbell (Nude inside) photographed by David LaChapelle Interview
Ben Affleck by Playboy
Features
Holiday Contributors: Wynton Marsalis, Donald Westlake, Leroy Neiman & More
Naomi Campbell Incredibly Nude
City Girls: Oral Sex, Wild Talk: They Are Hot And They Are Out There
The Search For Playmate 2000: Did We Find Her?
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