Starting in 1988, he has regularly been called upon to sing the national anthems at Boston Red Sox, Toronto Blue Jays and Toronto Maple Leafs games. From 1984 through 1992, he worked as a circulation representative for the Toronto Sun; Conrad Black heard him singing at company parties. Black, along with other executives, financed McDermott's independent recording of "Danny Boy" in 1992, which was picked up and released in North America by EMI Music Canada. Following this unexpected success, McDermott decided to pursue a professional singing career.