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.
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".