 | Playmate of the Month: Carrie Radison, photographed by Desmond Russell Playboy’s Stage Door Playmate | A fair filly from Philly tries her luck on the Great White Way |
| Dear Playboy | |
| Playboy After Hours | |
 | Fiction: The Fly | If she looked upon the horror any longer she would scream for the rest of her life, by George Langelaan |
 | Jazz: Rock ‘N’ Roll | Is this frantic phenomenon a new school of jazz?, by Leonard Feather |
 | Playmate Of The Year: Winters, The Winner | A shy, shapely Lisa tops the popular Playmate poll, photos by Bunny Yeager |
 | Article: Contour Contact | The gentle art of laying hands on lasses all about you, by Harrison Case |
 | Fiction: The Double Cross-Up | East, west, home’s best, by T.K. Brown III, illustrated by Seymour Fleishman |
 | Food: The Breaking Of The Fast | Morning menus for two, by Thomas Mario, photographed by Morton Shapiro |
 | Quiz: Further Puzzles Of Love And Passion | In which cupid’s shafts attain the shape of question marks, by Harlan Draper |
 | Attire: White’s Right | Where to bet your bottom dollar, by Blake Rutherford |
 | Humor: Playboy’s Party Jokes |
 | Humor: One For The Book | Presenting that clown prince of fun, Jerry Collins, by Arthur Kober |
 | Entertainment: A Real Free-Form Guy | The egghead humor of Mort Sahl, by Rolf Malcolm |
 | Ribald Classic: The Lady And The Angel | An ironic excerpt from The Revolt of the Angels by Anatole France, illustrated by Leon Bellin |
 | Satire: Enter The Handsome Stranger | Recipe for comic chaos: To baby doll and the rainmaker, add a pinch of Shakespeare, by Ray Russell |
 | Pictorial: The Back | Vikki Dougan makes marvelous exits, by Sam Baker |
| Playboy’s International Datebook, by Patrick Chase |
 Al Stine |  Alden Erikson |  Arnold Roth |  Gardner Rea |
 John Dempsey |  Phil Interlandi |  Arnold Kohn |  Jack Cole |
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Pipe and PJs 