13. Joe Francis – Girls Gone Wild? Really?
When you make your living being a total sleazeball, chances are that your choices are going to come back to haunt you eventually. That’s exactly what happened to Joe Francis, who, you may remember, was once the king of the world. Or at least he was the king of the softcore, totally ridiculous Girls Gone Wild empire. It’s amazing to me that this thing was as popular as it was, but Francis found the perfect mix of hedonism and exuberance (on the part of his “subjects”) to make money with on late-night TV. Unfortunately for him, and fortunately for all of us who were sick of his antics, he was also found to be filming underage girls and avoiding his taxes. He owed the IRS millions upon millions when he filed for bankruptcy in 2013. He also went to jail for a while because of his dealings with the aforementioned underage stars of his videos.
12. 50 Cent – Richest Broke Man in Hollywood
Well, he got rich and he didn’t die trying, but 50 Cent wasn’t able to hold on to his fortune for very long. It was only 2015 when the big-time rap superstar was reportedly worth over $150 million. But that all changed pretty quickly for him. First, he ran into a bunch of bad investments. Sources don’t say quite what all those bad investments were, but rappers, like star athletes, tend to have large ‘possies’ with even larger wants. I’m not saying that was 50’s deal, but you never know. Then he had to settle a huge lawsuit about a leaked sex tape (I didn’t know anyone sued over those anymore!), and voila! Bankruptcy. Unlike some stars on this list, 50 Cent actually had a plan to pay off his debt, which was anywhere from $10 to $50 million and supposedly has done, so he is now out of bankruptcy (although still paying off debt).