8. 50 Cent
Even though famed rapper 50 Cent filed for Chapter 11 bankruptcy, he doesn’t seem to be taking it very seriously. 50 has posed for many photos with loads of cash since going bankrupt, and has spent tons of money at strip clubs. He has been seen at the Ace of Diamonds strip club in West Hollywood making it rain on his favorite dancers. He showed up to an After Dark pool party with a big wad of cash and left with none of it. The rapper filed bankruptcy the same day he made it rain because he had two huge judgments against him: a $5 million lawsuit that he owed to Rick Ross, and $17.2 million that he owed to the headphone company Sleek Audio.