While he was spending on going to trial in the '90s, Jackson was still making money. He was collecting about $75 million a year during that time from owning the rights to his music library, as well as that of the Beatles — which he bought for $47.5 million in 1985 — according to the Daily News. Still, he spent more than he made.

Paul McCartney and Michael Jackson. AFP/Stringer/Getty Images

Source: The Daily News, Business Insider