Fifty years after the death of James Bond creator Ian Fleming, the film franchise is booming and Bond has cemented his place as perhaps the modern British cultural icon par excellence (albeit with plenty of irony in there as well). Along the way, the Bond phenomenon has spawned a great range of books—from the highly academic to the trivial and fun—and drawn the attention of some truly great writers.

Many writers of high distinction stayed at Goldeneye, the house Ian built on Jamaica’s north coast in 1946. It was at Goldeneye that Ian lived for two months a year for the rest of his life and where he wrote all the Bond stories. In order to represent different ways to assess the cultural legacy of Fleming and Bond, the list below does not include these contemporaries of Ian and Ann Fleming. (The exception to personal books is the Ann Fleming letters, which are absolutely indispensable.)

10. James Bond Bedside Companion, by Raymond Benson. (1988)

The Fleming estate chose Benson to replace John Gardener in writing continuation Bond novels, and Benson published six novels between 1997 and 2003 as well as short stories. Along the way, Benson became a leading authority on all things Bond, from clothes, to cars, to gadgets to guns. His encyclopedic knowledge makes his lavishly illustrated Bedside Companion a must for hard-core fans and full of delights and surprises—and intelligent insight—for the more casual reader.

9. Licence to Thrill: A Cultural History of the James Bond Films, by James Chapman. (1999)

Film critic James Chapman locates the Bond movies in the tradition of the British Imperialistic spy thriller, a genre that had its heyday in the 1930s with films such as The Thirty Nine Steps and The Man Who Knew Too Much, however anachronistic this was by the post-imperial 1960s. It is a perceptive analysis of the films, including their construction of “Britishness,” as well as a look at the strategies employed to update and renew the formula without losing its essential parts.

8. The James Bond Phenomenon: A Critical Reader, ed. Christopher Lindner. (2009)

Linder’s book is a wide-ranging collection of academic essays on all things Bond, including the books, the films, the music, and even the video games. Included is Umberto Eco’s now wildly-dated 1966 Structuralist reading of the novels, as well as a more recent piece from 1998 on Miss Moneypenny and ‘the desperations of filmic feminism’ and the lesbianism of Pussy Galore. Even James Bond’s penis gets an essay of its own by Toby Miller, which includes the baffling line: “Sean Connery’s Bond was very much a spectator to his own, publicly shared penis.”

7. The Life of Ian Fleming, by John Pearson. (1966)

John Pearson worked with Ian Fleming on his Atticus column for the Sunday Times, so he knew Fleming well and clearly admired him. This gives this biography, published only two years after Fleming’s death, a warmth, intimacy and freshness that is unmatched elsewhere. Although Pearson was severely hampered by having to give Ann Fleming approval (thus there is no mention of Ian’s Jamaican lover Blanche Blackwell, a huge part of his later life), Pearson writes with a lightness of touch and pace that is in many ways appropriate to Fleming and Bond.

6. The James Bond Dossier, by Kingsley Amis. (1965)

Poet, critic, Booker-prize winning novelist and distinguished professor at both

Princeton and Cambridge, Kingsley Amis is a giant of post-war British literature. But he had a secret passion for Ian Fleming’s Bond novels. His James Bond Dossier is an affectionate and perceptive analysis of the novels, and—more widely—a plea for popular, generic fiction to be accepted on its own terms. Amis believed that Fleming deserved to be ranked alongside those giants of an earlier time: Jules Verne, Rider Haggard and Conan Doyle. As such, Amis’ book is the father of all subsequent works that take Bond seriously. In 1968, Amis wrote the Bond continuation novel Colonel Sun under the pseudonym of Robert Markham. It is still considered the best non-Fleming Bond effort.

5. Ian Fleming, by Andrew Lycett. (1995)

Lycett is an accomplished and celebrated literary biographer; his books on Kipling, Dylan Thomas and Wilkie Collins are close to definitive. He brings the same levels of research and insight to his book on Fleming, with no stone unturned. If sometimes the detail is overwhelming, this remains the most complete biography by some distance. For Lycett, Fleming is essentially a tragic figure, undone by his complicated personality, his inability at intimacy and his chronic alcoholism.

4. The Letters of Ann Fleming, ed. Mark Amory. (1985)

Ann Fleming, Ian’s wife from 1952 to the end of his life, is as fascinating a character as Ian himself. Fiercely intelligent, a crashing intellectual snob, and connected to pretty much everyone in the British political and artistic establishment, she was also a brilliant and witty letter writer. Her correspondents included Patrick Leigh Fermor, Evelyn Waugh, Cecil Beaton, Cyril Connolly, and of course Ian himself. She was the master of the sneery put-down (she complained about their Jamaica neighbour Noël Coward that “the deserts of pomposity between the oases of wit are too vast”), but the letters also vividly trace the story of her arguably disastrous and mutually-destructive relationship with Ian, from passion to terrible anguish. The letters are introduced, selected and, where necessary, explained by a superb editor, Mark Amory.

3. The Politics of James Bond, by James Black. (2000)

Black provides a meticulous reading of the novels and the films in the context of the national, and global, political situation. He is particularly good on Fleming’s relationship with the United States, as it comes across in the novels. Fleming—and Bond—loved the speed, efficiency and energy of America, but distrusted the modernity as well, and deeply resented the new US global hegemony, writing to Ann in 1947 about, “their total unpreparedness to rule the world that is now theirs.” And for Fleming, the betrayal at Suez was unforgivable.

2. In Churchill’s Shadow: Confronting the Past in Modern Britain, by David Cannadine. (2002)

Professor Sir David Cannadine is one of Britain’s foremost public intellectuals and writers on modern history, particularly empire. This collection of essays includes a brilliant analysis of Fleming’s awkward personality, the result of an upbringing “by turns upstart and establishment, puritan and unrespectable, privileged and deprived.” These contradictions carry over to the portrayal of Britain in the Bond novels, whose decline Fleming—in the person of imperial hero James Bond—treats with a fascinating mixture of regret and denial. There is also a superb essay on Fleming’s fellow arch-imperialist and Jamaican neighbour Noël Coward.

1. The Man Who Saved Britain, by Simon Winder. (2006)

The Man Who Saved Britain is the wittiest book written about Bond—at times laugh-out-loud funny—and Winder is one of the only authors to appreciate how fun and silly a lot of the Bond canon really is. (To the annoyance of fans, he declared the film of Live and Let Die a “mean-spirited and offensive shambles, too stupid really even to be racist, too chaotic to be camp.”) While mixing in a memoir of growing up in the grey and tawdry Britain of the 1970s, Winder takes up the themes of Cannadine’s Fleming essay to explore how the invention of Bond and his popularity grew out of the bewildering decline of Britain and the collapse of the empire in the decades after the Second World War. Bond was a fantasy of continuing imperial power, bestriding the world and saving the Americans from their enemies. That this became very quickly ever more fantastical and even knowingly ironic did not diminish the appeal. He also noted the perfect irony of Prime Minister Eden staying at Fleming’s Goldeneye Jamaica house when his health broke down during the shambolic Suez Crisis of 1956, now seen as the final death spasm of the British Empire: “At the zenith of national incompetence, the architect of that incompetence stays at the very house in which the greatest reassurance and palliative, the Robin Hood of British imperialists’ darkest hour, was created.”

Matthew Parker is the author of Goldeneye: Where Bond Was Born — Ian Fleming’s Jamaica, out now from Pegasus Books.