Acclaimed writer Paul Theroux and Singapore go way back. All the way to 1968, to be precise, when he started his four-year stint teaching in the English department of the then University of Singapore.

It proved to be a “bewitching” experience for the 73-year-old American, who’s one of the marquee authors gracing this year’s Singapore Writers Festival (SWF). In fact, he still has vivid memories of those days.

“It was still shaking off its colonial atmosphere. I met many locals who remembered the Singapore rubber estates, the Japanese invasion and occupation and the humiliation of the British in Changi Prison,” shared Theroux in an email interview. “And there was a lot of old Singapore architecture still standing and a great deal of traditional culture — the amazing funeral processions, with drums and cymbals, the alarming displays of gore at Thaipusam and bee hoon soup and laksa.”

The author of novels such as The Mosquito Coast and travel books such as The Great Railway Bazaar remembers fondly living in College Green off Bukit Timah Road (“I had no home phone for three years and it was very peaceful, writing in a house without a phone — and no air-conditioning either!”) and pointed out that his son, broadcaster and journalist Louis, was born at Gleneagles Hospital (“I have a soft spot for that part of town, too, and the Botanic Gardens”).

Ultimately, it was the novel Saint Jack that would cement the bond between Theroux and the country. Written in 1973, it followed the adventures of a pimp named Jack Flowers through the underbelly of Singapore — and, notoriously, was made into a film in 1979. Directed by Peter Bogdanovich and headlined by Ben Gazzara, it was shot on location in a cat-and-mouse game with the authorities. The subsequent ban in Singapore was lifted only in 2006, the same year a book chronicling the making of the film, entitled Kinda Hot and written by film critic Ben Slater, was released. The film will be shown at the SWF.

The book itself wasn’t banned, however, and for Theroux, it was a meaningful chronicle of the times. “Saint Jack is related to my vision of old Singapore. I wanted to write about what I saw and heard, because at the time I began the book, the bulldozers were destroying the shophouses and reconfiguring the small alleys and lanes. You’ll see there are many specific places mentioned in the book that no longer exist. I had hope that, as well as being a good story, it would be a historical document describing what Singapore once looked like,” he said.

The Singapore experience is only one part of the Paul Theroux adventure book. His latest travel book, The Last Train To Zona Verda, chronicles his adventures across Africa.

“I had wanted for many years to travel in Angola, which is a remote and very wealthy (with oil revenue) country, but one that had been at war with itself for decades,” he said.

Our email interview, too, was done as he was in the middle of another long project. “For the past two years, I have been travelling in and around the rural parts of the Deep South of the United States, which was — until I went there — like a foreign country to me, with a distinct culture and history. It has been one of the most enlightening journeys I’ve taken and I hope to finish writing about it later this year in the hope that the book will come in 2015.”

Train rides figure a lot in his most famous travel books — whether it’s across Asia (The Great Railway Bazaar), the Americas (The Old Patagonian Express) and the United Kingdom (The Kingdom By The Sea) — so you could say he’s got the pulse on this mode of transportation.

“China and India and Russia are committed to improving and expanding their railways, and there are many schemes to build railways in Africa. A trip on a train is effortless and exciting, with none of the stress of an airplane. The high speed trains in the USA have proven to be a success. A train offers many opportunities to socialise, too, which is ideal for the writer-traveller.”

Describing himself as a “fiction writer who writes non-fiction with his left hand”, his proverbial ambidextrous approach is a boon for his efforts regarding the latter. “It is a great advantage in travel writing to be able to describe the smell, the look, the feel of a place — and the peculiarities of speech; these are what fiction writers strive to achieve. It was a long apprenticeship for me,” said Theroux, who started off as a fictionist.

When travelling, there are certain things that he makes sure he takes along. He’s replaced the Swiss Army knife (“not a good idea in these paranoid times”) with a small Sony shortwave radio to be able to listen to the news at night (which he has since replaced with a new one four years ago from a shop along Orchard Road).

But, ironically, travel books won’t be on the top of his list because they “rarely prepare you for what you find on the road. And this is the greatest reason of all to travel — to find out first-hand what a place is like, what the people are like, and to cure prejudice or the notion of stereotypes”.

And for anyone wanting to take a leaf out of the Paul Theroux guidebook to travel writing, it’s perhaps better to skip the spas and five-star luxury accommodations.

“One of the paradoxes of the writing life is that the worst, most difficult trips yield the greatest, most original stories. Take Albania, for example. Doesn’t ring much of a bell, does it? But when I went there (as recounted in his Mediterranean book, The Pillars Of Hercules) — I was delighted by the weirdness and hardship of it all. ‘I had a wonderful time’ is not a recipe for a riveting chapter,” he shared.

The Singapore Writers Festival 2014 will be held from Oct 31 to Nov 9. For details, visit https://www.singaporewritersfestival.com. Theroux will hold a solo lecture and will be part of a panel discussion on Nov 8. He will also have a meet-the-author session and the movie adaptation of his novel Saint Jack will be screened on Nov 9.