RIP Hugh Hefner, Playboy founder and producer of ‘Saint Jack’, the film about Singapore’s seedy underbelly

Hugh Hefner, the silk pajama-wearing, pipe-smoking owner and founder of Playboy Magazine, died today of natural causes in his famous Playboy Mansion home in Los Angeles, leaving behind a hallowed publishing legacy and a business empire. Known as a consummate playboy — having assured Esquire in 2013 that he had slept with over 1,000 women — Hefner was also a strong supporter of the civil rights movement, LGBT equality and free speech.

Of course, his brand of decadence and sexual freedom wasn’t without criticism. In fact, due to its adult content and nude photo spreads, Playboy has been banned in Singapore since 1959 under the Undesirable Publications Act. Even its website Playboy.com has been blocked by the Media Development Authority since 1996, with no plans at all to lift Playboy’s prohibition even after the magazine decided to drop nudity from its print editions (it’s since reversed that decision).

But not many folks know that Hefner actually managed to penetrate Singapore in in a different way. In the ’60s, he set up Playboy Productions, a company that would later produce films made by the likes of Monty Python and Roman Polanski.

It also made a little-seen film directed by Peter Bogdanovich, director of The Last Picture Show. It was set and filmed in Singapore, and it was called Saint Jack.

With Hefner on board as an executive producer, Bogdanovich would adapt Paul Theroux’s 1973 novel of the same name, which depicts Singapore’s seedy past — one filled with prostitutes, pimps, gangs, and other unwholesome things one no longer associates with our squeaky clean metropolis.

As a film, Saint Jack was groundbreaking in some ways. It was the first Hollywood movie entirely shot on location in Singapore; it featured homosexual scenes; it featured trans women. Fun fact: Knowing the authorities would never allow the filming such risqué content, the team pretended that they were shooting a rom-com called Jack of Hearts. The then Ministry of Culture approved the script and granted Bogdanovich permission to start production.

Unsurprisingly, Saint Jack was banned in Singapore in 1980, with authorities citing the fact that there would be “excessive edits required to the scenes of nudity and some coarse language before it could be shown to a general audience”. The story follows the exploits of Jack Flowers, the pimp-with-a-heart-of-gold in Singapore who tries to enter a new venture of setting up his own bordello — but in the process, he clashes with Chinese triad members.

While authorities might’ve blamed the explicit content, we all know it was mainly banned because it depicted the fledgling country in a bad light.

The ban on Saint Jack was only lifted in 2006, when it received an M18 rating. Though the film never got the wide release Bogdanovich had hoped for (despite a glowing review by noted film critic Roger Ebert), it still remains a fascinating chronicle of the sights and sounds of Singapore in the late ’70s, with highlights including Bugis Street, which was a gloriously sleazy spot before it got cleaned up.

If you’d like to see what Singapore was like before it became Singa-bore, here’s the entirety — yes, the entirety — of Saint Jack on YouTube.



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