The Singapore Grip (1978)
by J.G. Farrell
J.G. Farrell, along with Salman Rushdie are the most Booker-y of the Booker Prize wining authors. Rushdie has TWICE won the "Booker of Bookers" for best of all the Booker Prize winners, both times for the 1981 novel Midnight's Children. Farrell, on the other hand, first won for the Siege of Krishanpur, and was retroactively awarded the 'lost" Booker, awarded because a change in the qualifying dates for the yearly award, several years back. Unlike Rushdie, Farrell did not become an international celebrity, but that may have been more due to his untimely death than any other reason.
The Singapore Grip is the third book in his Empire Trilogy, and the only one that didn't win the Booker Prize. The Singapore Grip, while powerful, is a bit ponderous compared to the other two titles in the trilogy. Specifically, Farrell dives deep into the economics of commodity protection on the Malayan peninsula in the early part of the 20th century in such detail that for large portions The Singapore Grip reads like a work of non-fiction, and a boring work of non-fiction at that.
Which is not to say that The Singapore Grip doesn't have it's moments. Starting with the title, which is a slang term for a kind of sex where the man lays flat on his back and the woman uses her interior vaginal muscles to induce orgasm. The meaning of the title is not revealed until late in the book, which leads me to believe that the title is meant to be a metaphor for the experience of the British Empire in Singapore on the eve of the successful Japanese invasion of the colony.
This parallel is drawn out by the extensive description of the Japanese invasion, and the comparative impotence of the British Command, assisted by the equally impotent Australian Command, who are depicted lacking adequate troops, materiel or any kind of strategic understanding that would have allowed them to defeat the Japanese. This being a book published in 1978, Farrell also has a Japanese army private as a character, to show the invasion from the perspective of a common Japanese soldier.