1966/09 -- Vol. 13 No. 9. 286 pages.

Contents include:

  • Playbill
  • Dear Playboy
  • Playboy After Hours
  • The Playboy Advisor
  • Playboy's International Datebook -- travel by Patrick Chase
  • The Playboy Forum
  • Playboy Interview: Timothy Leary
  • "Buddy-Buddy" -- Fiction by Garson Kanin
  • Jocelyn Lane -- Heiress Apparent -- Pictorial
  • "Rendezvous" -- Fiction by John Christopher
  • It's Superspa! -- Reportage by Herbert Gold
  • "The Gold of Troy" -- Fiction by Harry Mark Petrakis
  • Motorcycle Scavenger Hunt -- Modern Living
  • The Cold Society -- Article by Nat Hentoff
  • Instant Assignation -- Humor by Dayton Herzog and Fabio Vargas
  • Illini Eyeful -- Playboy's Playmate of the Month Dianne Chandler
  • Playboy's Party Jokes -- Humor
  • Modified Mod -- Attire by Robert L. Green
  • Nor Any Drop to Drink -- Article by James Dugan
  • Playboy's Pigskin Preview -- Sports by Anson Mount
  • M'Lord's Larder -- Food by Thomas Mario
  • "All to Scale" -- Fiction by Lawrence Durrell
  • Topless -- Article/Pictorial
  • The America's Cup -- Man at His Leisure by Leroy Neiman
  • A Matter of Triple Duplicity -- Ribald Classic
  • The History of Sex in Cinema -- Part 10: The Forties - War and Peace in Europe -- Article by Arthur Knight and Hollis Alpert
  • Back to Campus -- Attire by Robert L. Green
  • On the Scene -- Personalities features brief biographies with black & white photos of three personalities of the time over two pages, this issue: John Barry - Gordon McLendon - Edward Keating
  • Two page Vargas Girl "He tried everything--flowers, jewelry, candy, furs--and they all worked."
  • The Playboy Art Gallery -- Humor by Jim Beaman
  • Little Annie Fanny -- Satire by Harvey Kurtzman and Will Elder