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Playboy January 1966
 Holiday Anniversary Issue
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Playboy January 1966
Playboy's Playmate of the Month Judy Tyler photographed by Mario Casilli Interview Princess Grace by Playboy
Features Playboy Interview With Princess Grace Little Annie Fanny Playboy's International Datebook Playmate Of The Month: Redhead Judy Tyler!
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Playboy February 1966

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Playboy February 1966
Playboy's Playmate of the Month Melinda Windsor photographed by Tony Marco Interview Federico Fellini by Playboy
Covergirl Sissy (nude inside) photographed by Larry Gordon Features A Provocative Pictorial On The Girls Of Rio The Latest In Stereo And TV Equipage Vladimir Nabokov, James Farmer, and William Saroyan Playboy Jazz Poll Winners
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Playboy March 1966

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Playboy March 1966
Playboy's Playmate of the Month Priscilla Wright photographed by Mario Casilli Interview Bob Dylan by Playboy
Covergirl Femlin Sculpture by Austin Fox (not nude) photographed by J. Barry O'Rourke Features "Octopussy" - Beginning A Previously Unpublished Ian Fleming Adventure Three Fresh European Sex Sirens Playboy's Party Jokes Di Donato & Hentoff
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Playboy April 1966

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Playboy April 1966
Playboy's Playmate of the Month Karla Conway photographed by Paul Morton Smith And R. Charleton Wilson Interview George Lincoln Rockwell by Playboy
Covergirl Cynthia Maddox (nude inside) photographed by Pompeo Posar Features Concluding Ian Fleming's James Bond Novelette "Octopussy" An Explosive Interview With Neo-Nazi Rockwell Spring And Summer Fashion Forecast Also, A Behind The Scenes Uncovering Of The layboy Covers And The Girls Who Adorable Adorn Them
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Playboy May 1966

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Playboy May 1966
Playboy's Playmate of the Month Dolly Read photographed by Pompeo Posar Interview Arthur Schlesinger, Jr. by Playboy
Covergirl Allison Parks (nude inside) photographed by J. Barry O'Rourke Features Playmate Of The Year Bunny From Britain: Playmate Of The Month Capital Punishment Article By Michael Disalle Jo Collins In Vietnam
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Playboy June 1966

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Playboy June 1966
Playboy's Playmate of the Month Kelly Burke photographed by William V. Figge Interview Mike Nichols by Playboy
Covergirl Mary Warren (nude inside) photographed by J. Barry O'Rourke Features The Girls Of Texas My Father & His Gangsters by Herbert Gold The Bogart Boom By Tynan & Crowther Freckle-Faced Playmate Of The Month Kelly Burke
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Playboy July 1966

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Playboy July 1966
Playboy's Playmate of the Month Tish Howard photographed by Bill Figge and Ed Delong Interview Ralph Ginzburg by Playboy
Covergirl Penny James, Patti Reynolds, Joann Russell, Barbara Shaw and Joey Thorpe (nude inside) photographed by Larry Gordon Features Further Adventures, Already, Of Secret Agent Oy Oy 7 An Interview With Ralph Ginzburg Pictorials On Ursula Andress And Sean Connery Red China, The U.S. And The U.N.
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Playboy August 1966

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Playboy August 1966
Playboy's Playmate of the Month Susan Denberg photographed by Peter Gowland Interview H.L. Hunt by Playboy
Covergirl Sissy (not nude) photographed by Don Bronstein Features Bunnies Of Dixie "The Death Of God" By Rev. William Hamilton The Manuscript of Doctor Arness by Gahan Wilson Jane Fonda In The Buff
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Playboy September 1966

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Playboy September 1966
Playboy's Playmate of the Month Dianne Chandler (covergirl) photographed by Pompeo Posar Interview Timothy Leary by Playboy
Features LSD's Leary Interviewed! College Fashion & Football Previewed! Toples Craze Reviewed! Authors Galore! Kanin, Hentoff, Petrakis, Durrell, Gold & Many More!
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Playboy October 1966

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Playboy October 1966
Playboy's Playmate of the Month Linda Moon photographed by Stan Malinowski Interview Mel Brooks by Playboy
Covergirl Penny James (not nude) photographed by Larry Gordon Features Ann-Margret As Modern Art Sex Stars Of The Forties Shakespearean Photo Satire New Fiction By Ray Bradbury
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Playboy November 1966

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Playboy November 1966
Playboy's Playmate of the Month Lisa Baker photographed by Bill Figge Interview Norman Thomas by Playboy
Covergirl Sue Batchelor (nude inside) photographed by Pompeo Posar Features The Sexual Freedom League Playboy Interview With Norman Thomas The Nudest Look In Feminine Fashions Ribald Classic: The Merry Nights Of Mistinguette
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Playboy December 1966
 Gala Christmas Issue
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Playboy December 1966
Playboy's Playmate of the Month Sue Bernard photographed by Mario Casilli Interview Sammy Davis Jr. by Playboy
Covergirl Nancy Gould (nude inside) photographed by J. Barry O'Rourke Features Fact And Fiction By James Baldwin The Girls Of Tahiti Playboy On The Town In London A Beginning New Spy Novel By Len "Ipcress File" Deighton
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