Ian Fleming: The Complete Man by Nicholas Shakespeare

Who would have guessed that the creator of James Bond might issue from the world of Bertie Wooster? Yet if you read Nicholas Shakespeare’s prodigiously researched biography of Ian Fleming, you find yourself in a world of toffs-about-town and boarding-school pranks worthy of the Drones. Britain’s head of intelligence in Paris in 1940 rejoiced in the name of “Biffy” Dunderdale. At the embassy in Lisbon, Fleming was pals with “Boofy” Gore.

Loelia Westminster (née Ponsonby)—one of the writer’s many old flames—recorded in her diary one day in 1940, “Hitler invaded Holland & Belgium. Bombed Brussels also many towns in France. Spent my time playing tennis at Selfridges.” No wonder Fleming’s fellow Old Etonian and man of letters Cyril Connolly likened the friend many took to be a devil-may-care bounder to “the hero of a Wodehouse novel.”

Yet it is the crafty genius of Shakespeare’s surely definitive account to suggest that Fleming had, in spades, the upper-class Brit’s gift for concealing both his talents and his intelligence. Not only could he recite large swatches of The Magic Mountain (in German) and write to Carl Jung to get permission to translate a talk on the 16th-century Swiss physician Paracelsus; he played a substantial part in winning the war—and then in protecting the peace that came after through the journalist-agents he sent around the globe as foreign manager of The Sunday Times.

“Hitler invaded Holland & Belgium. Bombed Brussels also many towns in France. Spent my time playing tennis at Selfridges.”

During his six years in naval intelligence, as Shakespeare informs us, Fleming organized covert operations in Nazi-occupied Europe and North Africa and was one of fewer than 30 people with access to the decryptions generated at Bletchley Park; he claimed, quite plausibly, to have drafted the original charter of the Organization of Strategic Services in the U.S., which would become the C.I.A. And Camelot was so besotted with James Bond (even Jackie) that it appears that many of the C.I.A.’s wackiest plots, as well as J.F.K.’s Cuban policy, came straight from Fleming or his creation.

Yet even as the scrupulously reticent soul refused to talk much about his greatest achievements, he came to be known for dreaming up a rather empty smoothy who had in fact a far less distinguished career, especially when it came to intelligence, than his maker. Fleming’s curse, Shakespeare suggests, is that he always felt overshadowed: by his war-hero father, who died in combat; by his golden-boy elder brother Peter, who won fame through books describing daring adventures from Brazil to Tashkent; and even by his grandfather, who had risen from a slum in Dundee to a 110,000-acre estate.

At some level, he produced books he could look down upon—his “great annual cowpat” is how he referred to the winter frolic he sent every year to his publisher—so he wouldn’t have to risk looking serious.

Ian Fleming had, in spades, the upper-class Brit’s gift for concealing both his talents and his intelligence.

It is, throughout, a melancholy tale. The man we associate with Aston Martins and martinis shaken, not stirred, lost his father when he was eight. His mother, in Shakespeare’s typically zesty characterization, was “imperious, melodramatic, entitled, and a narcissist.”

Fleming and his wife, Ann, at Goldeneye, their house in Jamaica, circa 1963.

When Fleming finally married, at 43, his socialite wife, Ann, not only filled the house with intellectuals who mocked her husband but carried her flirtations far beyond the dining room. In 1956, even as the prime minister, Anthony Eden, was coming to recuperate from the Suez crisis in Fleming’s celebrated house on the beach in Jamaica, Goldeneye, Ann Fleming was in bed with the leader of the opposition, Hugh Gaitskill, in the Hôtel Beaujolais in Paris.

The final sorrow came when Fleming made Bond, and Bond, in a sense, made Fleming. Suddenly, the solitary man most at home on the golf course was receiving more attention than he knew what to do with. Many of his friends were convinced that Bond in some senses murdered Fleming, as everyone closely associated with 007 somehow ended up in litigation, Fleming twice. The author of Chitty-Chitty-Bang-Bang died, at 56, on the 12th birthday of his only child, Caspar, and Caspar himself would take his own life 11 years later.

At some level, Fleming produced books he could look down upon—“my great annual cowpat” is how he referred to them—so he wouldn’t have to risk looking serious.

For all that bitter arc, Ian Fleming: The Complete Man is spiced with delicious tidbits on every page. Fleming sketched the story for what would become the hit TV show The Man from U.N.C.L.E. The film of Dr. No premiered not in New York or L.A. but at an Oklahoma drive-in; it went on to earn 60 times its budget. And—almost impossibly—the celebrated theme music for the Bond movies was drawn from an abandoned Peter Brook musical based on V. S. Naipaul’s novel A House for Mr. Biswas.

Fleming with Sean Connery on the set of Dr. No, 1962.

A seasoned novelist (The Dancer Upstairs) as well as a complete biographer, Shakespeare is ready to track down the names of 30 people said to have been the basis for James Bond, and to tabulate every other reference to flagellation in the novels. Best of all, he serves up a rich and fully fleshed portrait of the small world of born-to-the-manner Brits who all but controlled a quarter of the globe in the first half of the 20th century, deciding the fate of nations in their London clubs or Caribbean hideaways.

Fleming famously worked his way through dozens of women, yet seemed most at home in the company of men. He was born to a family that owned one of London’s biggest merchant banks, yet he insisted on living in spartan quarters with schoolboy cooking. Among the 450 men he commanded in war—the last gasp of the great British amateur—were a beaky-nosed Arctic explorer, a banjo player “known for his aversion to swearing,” and a butterfly collector.

Close friend to John le Carré and sterling biographer of Bruce Chatwin, Shakespeare knows just how to keep up with elusive characters who keep their secrets to themselves. But where le Carré created a kind of ideal father in Smiley (donnish, loyal, and honest), Fleming fashioned a fantasy alter ego. And where Chatwin was an attractive writer undone by all the lies he spun in life, Fleming comes across as a shy writer devoured by the winning character he created on the page.

By story’s end, it’s hard to tell how much it was a comedy, how much a tragedy, that so much, in war and peace, was being determined by Greek-spouting bons vivants who acted as if they had gone to school with Gussie Fink-Nottle.

Pico Iyer is a Columnist at AIR MAIL. He is the author of several books, including, most recently, The Half Known Life: In Search of Paradise and the upcoming Aflame, to be published in January 2025