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 Holiday Anniversary Issue
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Playboy January 1990
Playboy's Playmate of the Month Peggy McIntaggart photographed by Arny Freytag Covergirl Joan Severance (Nude inside) photographed by Mark Abrahams Interview Tom Cruise by Playboy
Features Tom Cruise Gets Intense: Don't Miss This Interview Sizzling Hollywood Newcomer Joan Severance In A Sultry Pictorial Decade Delirium! So Long To The Eighties, Hail To The Nineties (They're Going To Be Hot) Great Warhol! Andy's Divine Playboy Art
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Playboy February 1990
Playboy's Playmate of the Month Pamela Anderson photographed by Stephen Wayda and Arny Freytag Covergirl Bogna (Nude inside) photographed by Stephen Wayda Interview Eddie Murphy by Playboy
Features Mission: Implausible by Jeff Cohen The Women Of Russia: From Inside The U.S.S.R., A Naked Look At Glasnost Jim & Harry's Totally OK Adventure In Belize The Year In Sex
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Playboy March 1990
Playboy's Playmate of the Month Deborah Driggs photographed by Richard Fegley Covergirl Brandi Brandt & Donald Trump (not nude) photographed by Stephen Wayda Interview Donald Trump by Playboy
Features Cars 1990: We pick the hottest, sharpest, sexiest Rock And Racism: Has The Dark Side Taken Over Pop Music? Fax 'N' Figures: Sex Comes To The Electronic Office World-Class Playmates From Our Far-Flung Empire
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Playboy April 1990
Playboy's Playmate of the Month Lisa Matthews photographed by Arny Freytag Covergirl Deborah Driggs (Nude inside) photographed by Stephen Wayda Interview Stephen Hawking by Playboy
Features Girls Of The A.C.C. Tony Curtis' Daughter Makes A Smash Debut Love And Lust: Why Men And Women Are So Hit-And-Miss James Spader Made Easy by Jerry Lazar
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Playboy May 1990
Playboy's Playmate of the Month Tina Bockrath photographed by Arny Freytag and Pompeo Posar Covergirl Margaux Hemingway (Nude inside) photographed by Arny Freytag Interview Dave Barry by Playboy
Features Margaux Hemingway: Papa Said, Flaunt It! 20 Questions with Jennifer Tilly Profile: John Malkovich Music Winners: Results Of Our Biggest Poll Ever
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Playboy June 1990
Playboy's Playmate of the Month Bonnie Marino photographed by Richard Fegley and Kim Mizuno Covergirl Reneé Tenison (Nude inside) photographed by Francis Giacobetti Interview ThirtySomething by Playboy
Features Playmate Of The Year Rene? Tenison Interview: Great Talk From TV's Talkiest Show, ThirtySomething Mickey Rourke And Carr? Otis Are On Fire In Wild Orchid Plus: Mexico For Lovers, Horse Racing For Fun And Profit, Bikes For The Nineties And Much, Much More
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Playboy July 1990
Playboy's Playmate of the Month Jacqueline Sheen photographed by Stephen Wayda Covergirl Sharon Stone (Nude inside) photographed by Stephen Wayda Interview Quincy Jones by Playboy
Features Aaron Neville gets to the promised land Fighting the wrong war by Robert Stone Behind The Scenes With TV's Raunchiest Family What Men Risk For Love, By Asa Baber
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Playboy August 1990
Playboy's Playmate of the Month Melisa Evridge photographed by Richard Fegley Covergirl Erika Eleniak (Nude inside) photographed by Stephen Wayda Interview Larry King by Playboy
Features Baywatch Star Erika Eleniak In A Torrid Pictorial Larry King Interview: The King Of Talk Mouths Off Ultimate Softball! The Blue-Collar Game Takes Over Special! The Girls Of Canada
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Playboy September 1990
Playboy's Playmate of the Month Kerri Kendall photographed by Stephen Wayda Covergirl Rosanna Arquette (Nude inside) photographed by Greg Gorman Interview Rickey Henderson by Playboy
Features Rosanna Arquette Pictorial The Playboy Interview: Rickey Henderson Craig Vetter Boings From A Bridge Rabbit At Rest, By John Updike
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Playboy October 1990
Playboy's Playmate of the Month Brittany York photographed by Arny Freytag Covergirl Melissa Evridge (Nude inside) photographed by Stephen Wayda Interview Shintaro Ishihara by Playboy
Features School Daze! Party With The Girls Of The Big West Fearless Predictions! College Football's Best And Worst Buster Douglas Makes His Mark Straight Talk From Japan's Number-One America Basher, Shintaro Ishihara
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Playboy November 1990
Playboy's Playmate of the Month Lorraine Olivia photographed by Arny Freytag Covergirl Mickey MacKenzie (Nude inside) photographed by Stephen Wayda Interview Leona Helmsley by Playboy
Features Teri Copley: The Star Of We Got It Made Is Made For Us John Sununu Takes Charge Leona Helmsley Interview: "The Bitch" Fights Back A Hot Year For Sex In Cinema
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 Gala Christmas Issue
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Playboy December 1990
Playboy's Playmate of the Month Morgan Fox photographed by Stephen Wayda Covergirl Sherilyn Fenn (Nude inside) photographed by Barry Hollywood Interview Jay Leno by Playboy
Features Fenn Fatale: Twin Peaks' Sherilyn Fenn Jay Leno Interview: Hard Work, big Money And The Problem With Andrew Dice clay The Women Of Peter Jennings Leggy, Bosomy And Hot-Blooded: The Birds Of Great Britain
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