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Born Antonio Rosario Monopoli in Adelaide, Australia, he was a regular on the national radio show Kangaroos on Parade at the age of nine. At the age of sixteen he became a Carmelite monk and remained in the order for five years. He was appearing at Caesar's Palace in Luton when he auditioned for Opportunity Knocks, a British television talent show, which he won on six consecutive occasions in the 1970s.
In a national pre-selection to choose the song that would go to the Eurovision Song Contest, held on 9 March 1977 at the New London Theatre, Monopoly earned 66 points and placed ninth with the tune "Leave a Little Love." In 1976, his self-titled album peaked at No. 25 in the UK Albums Chart.
By the early 1980s, Monopoly was frequently obliged to display his talents aboard cruise liners. "I lived on one yacht for a year," he said. "I went to 56 countries. I had champagne for breakfast. But I hated it".
When fulfilling his increasingly rare engagements on dry land, he divided his time between Australia and the UK. He was headhunted for a musical while appearing in Cinderella at Hanley, near Stoke-on-Trent. Monopoly starred – in drag – in Moby Dick, the inaugural production at the newly refurbished Old Fire Station Theatre in Oxford. The show's success prompted Cameron Mackintosh to mount a 1992 West End production, which opened to scathing reviews and promptly closed, after which Monopoly portrayed Old Deuteronomy in a UK tour of Cats.