 | Playmate of the Month: Madeline Castle, photograph from Jack and Jean Drebert, ACA Miss October |
| Dear Playboy | |
 | Fiction: Appearance and Reality | The senator opened the door and found his mistress in bed with a stranger. And the stranger was wearing the senator’s pajamas!, by W. Somerset Maugham |
 | Humor: College Drinking Songs | To be sung with good fellows and plenty of brew |
 | Satire: Hollywood and the Gladiators | Excited by the current rash of Roman films, Playboy has decided to produce one of its own, by Ray Russell |
 | Article: The Art Detective | Sheldon Keck matches wits with men like Michelangelo |
 | Games: Drink Quiz, by Joseph C. Stacey |
 | Sports: Block That Yok! | Selected from his book of sports stories, “Now I’ll Tell One”, by Jack Strausberg |
 | Humor: Playboy’s Party Jokes |
 | Satire: How to Write Memos | More on how to succeed in business without really trying, by Shepherd Mead, illustrated by Claude Smith |
 | Fiction: Old Shep | When my roommate got his girl into trouble, I tried to help them, but it was his dog, Shep, that finally got them out, by Jack W. West, illustrated by Al Stine |
 | Humor: Boola Boola!, by Julien Dedman |
 | Article: Later-Comma | A fascinating word-game for lovers of good literature on those dull evenings when you haven’t a damed thing worth while to do, by G.M. White |
 | Humor: Campus Canines |
 | Food: Is She Your Kind of Dish? | How to read menus and the feminine mind, by Thomas Mario |
 | Pictorial: Nudity and the Foreign Film | U.S. censors keep busy cutting the sin out of Europe’s cinema |
 | Ribald Classic: Tale of the Toe | A new translation of one of the choicest stories from Boccaccio’s Decameron, illustrated by Leon Bellin |
 Al Stine |  Arv Miller |  Jack Cole |  Richard Loehle |
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Pipe and PJs 