He made his fortune in advertising, has been married six times and likes to shout whole racecourses drinks when one of his horses wins.
But the dark side of John Singleton's larrikin image has spilled into public view after he lunged at one of his closest friends with a broken wine glass. The dramatic scenes - captured on camera and splashed across the pages of an Australian newspaper - came at the end of a boozy three-hour lunch in an upmarket Sydney restaurant on Monday afternoon.
For a few moments the prominent businessman known as Singo became Swingo, as he smashed a wine glass and lashed out at billionaire Jack Cowin, the founder of Hungry Jack's fast-food chain.
Yesterday both men tried to laugh off the ugly scenes, but NSW Police are looking into "the circumstances surrounding the incident". The investigation comes a year after casino mogul James Packer and TV network boss David Gyngell brawled on a pavement in nearby Bondi. Both received A$500 ($539) fines.
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Sydney's latest "big end of town" biffo reportedly erupted after the 73-year-old took umbrage at Cowin, 72, mocking him for drinking rose wine rather than beer. Insisting it was a joke, Singleton yesterday admitted the photos - sold to Sydney's Daily Telegraph for a reported A$10,000 - did not "look funny".
He told one TV reporter that he smashed the glass and "simulated glassing" before Cowin got up and pretended to choke him by the throat.
"We all laughed and sat down and had another little drink. Jack and I have been mates for 50 years and our common denominator is that we like bagging one another, playing tricks on one another."
Cowin told the Australian "it was just people having a laugh". "It has been picked up and made into something it wasn't."
The businessmen had enjoyed a long lunch at Kingsleys Steak and Crabhouse on Woolloomooloo's Finger Wharf with Singleton's son, Jack, former Noiseworks singer Jon Stevens and ex-American football star Colin Scotts.
The photos show Singleton being restrained by restaurant manager Sinead Murtagh as he stands over Cowin brandishing the broken glass.
After leaving the establishment, Singleton told the cameraman that it had been a "fight over a woman" and launched into an X-rated rant that was caught on video. He joked that Stevens - recently accused of assaulting ex-fiancee Jodhi Meares - was "trying to find a woman to belt, and I was trying to have a sex change so he could bash me." Asked for his view on violence, Singleton charged the cameraman, shouting repeatedly: "I f***ing love it." He was then carried by Stevens and Scotts into a pub, where he stayed until being picked up by his chauffeur more than two hours later.