11. Michael Jackson: $350 million
At its peak, his empire was vast—he was earning $50 million a year through the 1980s and 1990s. In 1985, with one of the biggest-selling albums ever (Thriller sales have beeninflated, but the 66 million copies were sold worldwide), a series of incredibly lucrative tours, and a record $5 million deal with Pepsi (worth $11 million today), the questionable investments started coming quickly. He dropped $47.5 million to buy ATV Music ($101 million today), 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 (a total of $111 million today). By 2003, he held $200 million in debt, and even that wasn’t enough to break him.
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