Hugh Hefner and James Bond: their forgotten connection
By David Pegram

With Hugh Hefner’s passing on September 27th, many media outlets have paid tribute to a man widely known as the founder and managing editor of Playboy. But few realize that there has been a long-standing connection between Hefner’s prized publication and the world of James Bond.
One only need to revisit
On Her Majesty’s Secret Service
to see this connection on full display — so to speak. While waiting to crack a safe in Bern law office, Bond comes across a copy of the February 1969 issue of
Playboy
. He takes a look at the magazine’s centerfold, and an amused smile comes across his face. (Interestingly, the same issue was used as a prop on
Mad Men
).
Had Bond found an older edition, he might have been reading about himself. Indeed, it was Playboy that first published Ian Fleming’s James Bond short story, “The Hildebrand Rarity,” about Bond’s encounter with millionaire Milton Krest (not the same Milton Krest as in Licence to Kill).
Since that 1960 publication, Bond short stories and serials became a regular occurrence in Playboy. In fact, a serialized version of On Her Majesty’s Secret Service appeared in the magazine in 1963. The most recent Bond fiction to appear in the magazine was in 1999, with Raymond Benson’s original piece, “A Midsummer Night’s Doom.” The story is about James Bond’s visit with Hugh Hefner (yes, you read that correctly).
Over the course of those years,
Playboy
also featured spreads of Bond girls, including a 1977 shoot of Barbara Bach and a 1979 pictorial on the women of
Moonraker.
Sorry, no photos available for those.
But the James Bond connection has existed beyond the magazine. In Diamonds Are Forever, Tiffany Case finds Bond’s wallet (which Bond placed upon the deceased Peter Franks). There, she takes out, of all things, a Playboy Club membership card, Nobody should be surprised by this.
With Hefner’s passing, who knows if Bond will ever be featured in Playboy again. Maybe it will happen again…for nostalgia’s sake.