Harry Nilsson was making millions at the height of his career, but he was sadly penniless when he died at just 52 years old. The singer-songwriter signed a record deal worth $5 million at the height of his career, but the money was gone by the time he died. Harry Nilsson was making millions at the height of his career, but he was sadly penniless when he died at just 52 years old. The singer-songwriter found fame in the 1970s with his album Nilsson Schmilsson and at the height of his career, he signed a record deal worth $5 million....