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PLAYBOY and James Bond An Iconic Collaboration in Lifestyle and Espionage

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Since its inception in 1953 by Hugh Hefner, PLAYBOY magazine has been synonymous with not just glamour and the celebration of the female form, but also with cutting-edge journalism and literary contributions. Among its most notable collaborations is with Ian Fleming’s James Bond, which not only elevated the magazine’s cultural status but also enriched the Bond saga with an American twist. We take a look at some of the key PLAYBOY and James Bond related issues which included new stories, serialized novels and interviews.

Playboy Magazines related to James Bond including April 1965, November 1965, June 1967, July 1979 and September 1987. Sold for Ewbank’s, April 2021.

One of the earliest intersections of PLAYBOY and James Bond occurred in the March 1960 issue, which featured the first publication of The Hildebrand Rarity, a short story by Fleming. This issue was particularly special as it predated the UK hardcover release, marking PLAYBOY’s role in introducing Bond to American readers. The story was accompanied by an illustration by Allan Phillips, enhancing the visual appeal and giving readers their first taste of Bond’s adventures in print.

Playboy Magazine March 1960 with Ian Fleming The Hildebrand Rarity
Playboy Magazine March 1960 with Ian Fleming story The Hildebrand Rarity. This good copy sold for £13.50 on ebay, April 2024.

PLAYBOY’s relationship with Bond deepened as it serialized entire novels. In April 1963, On Her Majesty’s Secret Service was serialized, a significant move that coincided with the hardback release in the UK. Illustrated by Robert Weaver, the serialization featured distinctive artwork that, despite depicting Bond with a Sean Connery-like visage, added a unique flavor to Fleming’s words.

Playboy April 1963 James Bond On Her Majesty's Secret Service
Playboy April 1963 James Bond On Her Majesty’s Secret Service. As with all magazines and books condition is key. Fine examples are estimated at £20-£40.

The magazine also became a cultural hub for Bond fans through its interviews and features with Bond actors. Notably, in November 1965, amidst the height of Bondmania triggered by the release of Thunderball, PLAYBOY published an extensive interview with Sean Connery. This issue not only discussed Connery’s portrayal of Bond but also included an iconic cover and a pictorial spread featuring various Bond girls, blending cinematic and narrative elements seamlessly.

Playboy November 1965 the James Bond issue
Playboy November 1965 the James Bond issue. This example sold for £24.99 on ebay, May 2024.

The February 1969 issue of PLAYBOY also holds a unique place in James Bond lore, as it appeared directly within a Bond film, “On Her Majesty’s Secret Service” released the same year. In a particularly meta moment, George Lazenby, playing Bond, is seen perusing a copy of this very issue during a scene set in the offices of a Swiss lawyer. This inclusion was not just a casual product placement; it served as a clever nod to the ongoing relationship between the James Bond franchise and PLAYBOY magazine. The issue itself is remembered for its timely content, which included features aligning with the style and ethos of the Bond series, though specifics about its articles and pictorials reflect the general thematic synergy between the magazine and the Bond films during that era. This particular instance of cross-promotion enhanced the suave, sophisticated image of Bond, while also solidifying PLAYBOY’s status as a publication at the forefront of popular culture and cinematic trends.

Playboy February 1969 On Her Majesty's Secret Service with Boutells Heraldry
Original Items George Lazenby as James Bond uses similar items in the film On Her Majesty’s Secret Service – the book on Heraldry when he is in disguise as Sir Hilary Bray and the Playboy magazine he takes the centrefold when he discovers the magazine in the offices of the Swiss Lawyers Gumbold. These two items sold for £150 at Coys, December 2015.

Furthermore, PLAYBOY often used its platform to introduce new Bond girls, ahead of their cinematic debuts, with pictorials that sometimes stirred as much attention as the films themselves. For instance, Jill St. John, who appeared in the March 1960 issue, later starred as Tiffany Case in “Diamonds Are Forever” (1971). Her role was famously linked back to the magazine when Bond, played by Sean Connery, presented a PLAYBOY Club membership card in a key scene, blurring the lines between the character’s fictional and real-world affiliations.

Over the decades, PLAYBOY continued to be a venue for Bond-related content, publishing stories and interviews that coincided with film releases and maintained the espionage allure. The magazine featured interviews with later Bond actors and continued to serialize Bond stories, such as “You Only Live Twice,” alongside stunning illustrations by artists like Daniel Schwartz, ensuring that the visual narrative of Bond was as compelling as the written word.

The PLAYBOY-Bond partnership also delved into retrospectives and special editions, such as the 1987 issue celebrating three decades of James Bond in PLAYBOY, showcasing past serialized stories and artwork. This demonstrated the enduring legacy of Bond in the magazine, highlighting how pivotal PLAYBOY was in shaping the American perception of the suave British spy.

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