1966/05 — Vol. 13 No. 5. 230 pages.

Contents include:

  • Playbill
  • Dear Playboy
  • Playboy After Hours
  • The Playboy Advisor
  • Playboy’s International Datebook — travel by Patrick Chase
  • The Playboy Forum
  • The Playboy Philosophy – Editorial by Hugh Hefner
  • Playboy Interview: Arthur Schlesinger, Jr.
  • “The Roach Powder in the Maple Walnut” – Fiction by Bernard Wolfe
  • Brava Costas! — Travel by Geoffrey Bocca
  • “The Master Copy” — Fiction by Frank Dobinson
  • Why Does My Art Go Boom? — Article by Len Deighton
  • The Case for American Wines — Drink by Thomas Mario
  • “The Eastern Sprints” — Fiction by Tom Mayer
  • Bunny From Britain — Playboy’s Playmate of the Month Dolly Read
  • Playboy’s Party Jokes – Humor
  • Snap Decisions — Modern Living by Vincent T. Tajiri with photos featuring Woody Allen showing off cameras and gear
  • “The Hayloft” — Fiction by Pietro Di Donato
  • Captial Punishment — Article by Michael Disalle
  • Boss Tweed — Attire by Robert L. Green
  • How to Be a Faquir — Article by Daniel P. Mannix
  • Playmate of the Year — Allison Parks Pictorial
  • The Cunning of Khalbas the Cuckold — Ribald Classic
  • Playmate First Class: Jo Collins in Vietname – Pictorial Essay
  • Lord Love a Teevie Jeebie — Satire by Shel Silverstein
  • Little Annie Fanny — Sature by Harvey Kurtzman and Will Elder
  • Vargas Girl – Two page spread – “I must admit that some undercover assignments are more interesting than others”
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