The King of Pop earned $50 million a year through the 1980s and 1990s.
In 1985, he already had one of the biggest-selling albums ever ("Thriller," which sold 66 million copies worldwide) a series of incredibly lucrative tours, and a record $5 million deal with Pepsi (worth $11 million today) to his name, and the questionable investments started coming quickly.
He dropped $47.5 million to buy ATV Music, which included the Beatles’ catalog (which Paul McCartney would later buy back at a bargain).
In 1987, he bought the “Neverland” ranch for $19.7 million and invested another $35 million in it. By 2003, he held $200 million in debt, but even that wasn’t enough to break him.