Michael Jackson

The King of Pop once had the most lucrative recording contract in the world. By 1991, it seemed like he had more cash than he, his kids, their kids and their grandkids couldn’t even spend it. But somehow, he did. Estimates vary around how much he was worth, but it’s somewhere between $750 Million and $1 Billion. Between all of his records, shows, endorsements and his ownership of The Beatles catalogue, he was supposedly set.

But when he died, he died in incredible debt – close to $500 Million. On top of his plastic surgery, love of drugs and his other legal troubles, what really drained his account was his irresistible love of crazy projects, from the Neverland Ranch to a theme park for cows.

The irony was that at the time of his death, he had a plan to get out of debt, and since then his estate’s been amassing close to $8 Million dollars a year.