50 Cent

The rapper and actor 50 Cent, whose real name is Curtis Jackson III, filed for chapter 11 bankruptcy in 2015 after a New York jury found him liable for $5 million for posting a sex tape of a rival rapper’s girlfriend on-line without her permission. This may have been the straw that broke the camel’s back as he was already in debt for several business deals that went South, including one to market headphones. He emerged from the bankruptcy by re-paying about $22 million in debt, $8.7 million of which came from his personal wealth and $13.65 million of which came from a legal malpractice suit he won against his non-bankruptcy lawyers.