1968/05 -- Vol. 15 No. 5. 226 pages.

Contents include:

  • Playbill
  • Dear Playboy
  • Playboy After Hours
  • The Playboy Advisor
  • The Playboy Forum
  • The Playboy Interview: Masters and Johnson
  • The Annex -- Fiction by John D. MacDonald
  • There Once Was an Indian Maid -- Julie Newmar Pictorial
  • Henne Fire -- Fiction by Isaac Bashevis Singer
  • Indy -- The Golden Brickyard -- Sports by Ken W. Purdy
  • Ulysses at Cannes -- Article by William Wiser
  • Casual Convertibles -- Attire by Robert L. Green
  • There's One Born Every Second -- Nostalgia by Daniel Mannix
  • Never Press the Lapels -- Fiction by Gerald Cleaver
  • Here Comes Miss Jordan -- Playboy's Playmate of the Month Elizabeth Jordan
  • Playboy's Party Jokes -- Humor
  • The Dead Astronaut -- Fiction by J.G. Ballard
  • Playboy's Guide to a Continental Holiday -- Travel by Len Deighton
  • The Snooping Machine -- Article by Alan Westin
  • Playmate of the Year -- Angela Dorian Pictorial
  • Vargas Girl -- "I don't mind of a man loves me and leaves me--as long as he leaves me enough"
  • The Virgin of Venice -- Ribald Classic
  • The Art of Composing a Meal -- Food and Drink by Thomas Mario
  • Exotica -- 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: John Conyers, Jr., The 5th Dimension, and Tom Stoppard