From Chicago nightclub to Mayfair salon, the Playboy Bunny became an emblem of the transatlantic age: part theatre, part discipline, and entirely of its time.
Hugh Hefner arrives in London with an entourage of Bunny Girls to officially open his new Playboy Club (June 1966).
Credit: Trinity Mirror / Mirrorpix
It began, as so many mid-century ideas did, with a man and a magazine.
When Hugh Hefner launched Playboy in 1953, he was not merely publishing photographs — he was constructing a world. A world of jazz and modernism, of strong cocktails and sharper tailoring — an American vision, filtered through a distinctly European lens.
Hugh Hefner surrounded by two dozen of the original Bunnies from the first Playboy Club in Chicago in 1960.
Credit: Everett Collection Inc.
From the outset, that world intersected with another emerging mythology: James Bond.
The association between Playboy and Bond is not anecdotal — it is structural.
Ian Fleming published several Bond short stories in the magazine, placing 007 directly within Hefner’s universe of cultivated sophistication. The Hildebrand Rarity appeared in March 1960 — as, coincidentally, did future Bond Girl, Jill St. John.
Playboy Magazine, March 1960 issue.
Credit: Playboy Enterprises Inc.
Playboy had already published a notably favourable review of Goldfinger in its October 1959 issue — an endorsement that, alongside John F. Kennedy’s praise for From Russia, with Love in Life magazine in 1961, helped propel the Bond novels into the American mainstream.
On Her Majesty's Secret Service was serialised in the April, May and June issues (1963).
Credit: Playboy Enterprises Inc.
The Property of a Lady followed in the January 1964 issue.
Credit: Playboy Enterprises Inc.
You Only Live Twice was serialised in April, May and June, 1964.
Credit: Playboy Enterprises Inc.
The Man With The Golden Gun was serialised in 1965.
Credit: Playboy Enterprises Inc.
Before its June 1966 hardback publication in the UK, Ian Fleming’s final short story, Octopussy, appeared in the March and April issues of Playboy magazine.
Credit: Playboy Enterprises Inc.
On screen, the relationship became knowingly self-referential. In On Her Majesty's Secret Service, George Lazenby is seen reading Playboy — a fleeting but telling detail.
George Lazenby studying the February 1969 issue of Playboy in On Her Majesty's Secret Service.
In the subsequent 007 movie, Diamonds Are Forever, Bond assumes the identity of diamond smuggler Peter Franks, switching wallets after dispatching him in the corridor of Tiffany Case’s apartment. Discovering the Playboy Club card, Tiffany gasps: “You’ve just killed James Bond.”
James Bond's Playboy Club membership card from Diamonds Are Forever (1971).
Off screen, the November 1965 issue of Playboy magazine had arrived in concert with the release of Thunderball that December. Inside, a candid and expansive interview with Sean Connery was accompanied by a 14-page feature, “James Bond’s Girls,” written by screenwriter Richard Maibaum, celebrating the leading women of the series’ first four films.
The November 1965 included a candid interview with Sean Connery (read here).
Credit: Playboy Enterprises Inc.
And then there were the Bond women.
Ursula Andress, whose emergence from the sea in Dr. No defined a generation, featured in the July 1965 issue. She was photographed by her then husband, actor and filmmaker John Derek, who would later lens Playboy pictorials for two of his future wives, Linda Evans and Bo Derek.
Ursula Andress photographed by John Derek for Playboy (July 1965).
Credit: Playboy Enterprises Inc.
The pattern continued with a succession of Bond Girls appearing in the magazine, extending their cinematic presence into print.
Bond Girls continued to appear in Playboy throughout the 1970s and 1980s.
Credit: Playboy Enterprises Inc.
One of the last Bond women to feature in Playboy was Daphne Deckers who — if unrecognisable here — appeared in Tomorrow Never Dies (1997).
Credit: Patti McConville
Not all accepted. Caroline Munro famously declined a £10,000 offer — an act of refusal that speaks as eloquently about control as any appearance: reportedly feeling that, "nudity is turning men away from women and that it is far more attractive and sexy to suggest rather than give away the mystery".
Caroline Munro refused to reveal all for Playboy (Dec. 1968).
Credit: Zuma Press Inc.
Bond did not merely appear in Playboy. He belonged there.
But: if Bond represented one axis of mid-century cool, The Beatles represented another — and Playboy intersected with both.
On 22 January 1965, having just taken residence at 34 Montagu Square, Ringo Starr attended a luncheon at Trader Vic’s in the London Hilton, seated alongside J. Paul Getty — then one of the richest men in the world. The occasion marked Getty’s fifth year as a contributing editor to Playboy, a detail that neatly captures the magazine’s reach across industry, culture, and media.
Ringo Starr and J Paul Getty at Trader Vic's (Jan. 1965)
Credit: Smith Archive
Ringo’s presence was prompted by a remark he had made while being interviewed with The Beatles for the magazine: that while he had little desire to meet the Queen, he would quite like to meet Paul Getty.
The wish, it seems, was granted.
Three years later, Ringo had sub-let the Montagu Square premises to John Lennon and Yoko Ono, where they staged the cover photograph for their Two Virgins album, a moment of artistic provocation that echoed Playboy’s own willingness to challenge convention.
The photograph that graced the cover of the Two Virgins album, but didn't appear in Playboy magazine.
Credit: Antiques & Collectibles
John and Yoko were later interviewed in the January 1981 edition of Playboy, bringing with them a more avant-garde strain of transatlantic influence.
Ironically, the cover of that edition featured Bond Girl, Barbara Bach, who married Ringo Starr three months after it was published.
Bond girl Barbara Bach before becoming Mrs Ringo Starr.
Credit: Playboy Enterprises Inc.
Before Bond, before The Beatles, there was one defining image.
Marilyn Monroe appeared on the first issue of Playboy, becoming — retrospectively — the magazine’s original icon. American, luminous, and enduring.
The cover of the first edition of Playboy magazine
Credit: Patti McConville
Hefner never entirely escaped that first image.
So much so that he later purchased the burial plot beside hers, ensuring that, in death as in life, the founder and his first star would remain forever linked.
Hugh Hefner (9th April 1926 - 27th September 2017)
Credit: Zuma Press Inc.
By the late twentieth century, the world had shifted.
The clubs faded. The codes loosened. Figures such as Anna Nicole Smith represented a different era — one less concerned with restraint, more aligned with the velocity of modern celebrity.
And yet, the image endures.
The Playboy Bunny was never merely decorative. It belonged to a transatlantic performance — where Bond, The Beatles, and Monroe shared the same stage... and the result was legend.