1969/06 -- Vol. 16 No. 6. 266 pages.

Contents include:

  • Playbill
  • Dear Playboy
  • Playboy After Hours
  • The Playboy Advisor
  • The Playboy Forum
  • The Playboy Interview: Gore Vidal
  • Downwind from Gettysburg -- Fiction by Ray Bradbury
  • The Paramilitary Right -- Article by Eric Norden
  • De Sade -- Pictorial
  • Two-page Vargas Girl -- "There's nothing wrong with premarital sex, as long as it doesn't hold up the cermeony."
  • The Grand Hotels -- Article by Robert Morley
  • High Water Marks -- Attire by Robert L. Green
  • The American Novel Made Us -- Article by Seymour Krim
  • Le Mans -- Man at His Leisure by Leroy Neiman
  • I Do Not Like Thee, Dr. Feldman -- Fiction by Henry Slesar
  • Hare Apparent -- Playboy's Playmate of the Month Helena Antonaccio
  • Playboy's Party Jokes -- Humor
  • Paella Y Sangria -- Food and Drink by Thomas Mario
  • The Risk Takers -- Article by Robert Daley
  • Gemini -- Fiction by Ray Russell
  • Playboy's Gifts for Dads and Grads -- Gifts
  • Playboy's Guide to Mutual Funds -- Article by Michael Laurence
  • A Life in the Day Of -- Fiction by Frank M. Robinson
  • Word Play -- Satire by Robert Carola
  • Playmate of the Year -- Connie Kreski Pictorial
  • Wanda Hickey's Night of Golden Memories -- Humor by Jean Shepherd
  • The Lady in Green Slippers -- Ribald Classic by Restif de la Bretonne
  • Breezy Does It -- Attire by Robert L. Green
  • Hostileman -- Satire by Jules Feiffer
  • On the Scene -- Personalities features brief biographies with black & white photos of three personalities of the time over two pages, this issue: Tom Jones, Arthur Ashe, and Buck Henry