Michael Bublé ($60 million)
Michael Bublé has a strange success story. He started as a struggling wedding singer until there was one particular wedding where Brian Mulroney, the aid to the former Canadian prime minister, watched him perform. Mulroney was so blown away by the performance that he gave Bublé’s CD to the prime minister himself, who hired Bublé to sing at his daughter’s wedding. Lo and behold, Bublé met his producer, David Foster, at that wedding and the rest is history. Due to his widespread commercial success, Bublé has earned himself roughly $60 million over the course of his short career.