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"