6. Curtis “50 Cent” Jackson

The hip hop king of the 2000s who has several Grammy nominations and a clothing line to his credit, 50 Cent was ordered to pay about $7 million to Lastonia Leviston in 2009, for releasing an adult video featuring her without her consent. Further in 2014 he was once again asked to pay about $16 million to Sleek Audio after an unsuccessful attempt at a business plan with the latter. All of this culminated in the rapper becoming bankrupt.