 | Playmate of the Month: Anne Flemming, photographed by Hal Adams A Is For Anne |
| Dear Playboy | |
 | Fiction: The Closed Shop | When the madams of a nation get together, let the president beware!, by W. Somerset Maugham, illustrated by Richard Tyler |
 | Jazz: Collecting Jazz | About discophiles, their records, and starting a collection of your own, by James H. Lavely |
 | Fiction: Spy Story | Bill didn’t mind being shadowed — but incompetent shadows were really the last straw, by Robert Sheckley |
 | Pictorial: Fair Forms And Foul Fiends | The magazines of yesteryear out-Mickied Spillaine |
 | Pictorial: Mixing The Perfect Martini | The secret of success is precision, by Stan Ceplius |
 | Article: The Big Bosom Battle | An eminent medico says “down with bosoms.” We say “down with necklines.” En garde, doc!, by Jay Smith |
 | Fiction: Mating Season | ‘Twas a green book and a gold-haired girl that brought the color to Terry’s face, and him not a wicked boy at all, al all, by Charles Lee Robinson |
 | Attire: The Basic Wardrobe | For fall and winter wear, a closetful of good taste, by Jack J. Kessie, illustrated by LeRoy Neiman |
 | Humor: Playboy’s Party Jokes |
 | Survey: The Playboy Reader | About the man who buys the magazine |
 | Entertainment: “The Sammy Davis Story” | His life would make a colossal Hollywood musical, by Eric Franklin |
 | Food: Audacious Italian Dishes | And we don’t mean Mangano or Lollobrigida, by Thomas Mario, illustrated by Morton Shapiro |
 | Pictorial: Pink Elephants And Purple Hair | New York press agents are painting the town |
 | Satire: The Top Of The Heap | The last word on how to succeed in business without really trying, by Shepherd Mead, illustrated by Claude Smith |
 | Ribald Classic: The Ring And The Garter | A new translation of a true episode from the Mémoires of Casanova |
 Al Stine |  Arv Miller |  Jack Cole |  Jack Cole |
 Larry Klein |  John Dempsey |  Ben Denison |
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