People often assume celebrities, with their lavish lifestyles and multiple properties, are financially stable people. And while that’s usually true, in the wise words of the late Notorious BIG: mo money mo problems. Unexpected medical bills, legal bills or simply becoming accustomed to a lifestyle that makes it difficult to pull back when times get tough are some of the biggest factors that lead high-profile figures to declare bankruptcy.

It is worth noting, however, that bankruptcy does not mean someone is completely broke. Often, it’s used as a legal protection against total financial insolvency, by “providing financial relief in the form of a restructured debt repayment plan or a liquidation of certain assets to pay off a portion of your debt,” according to . From to , we’ve compiled a list of 14 celebrities who lost their fortunes.

In 2004, years before Michael Jackson’s untimely death at age 50, that he was all but broke and would be unable to repay a $70m loan to the Bank of America. Despite his poor financial state, Jackson was said to have remained flippant about his luxurious lifestyle, continuing to rack up monthly bills of $2m on new cars and other items. At the time of his death in 2014, the “Thriller” singer owed more than court documents revealed.

, Sharon Stone recently revealed that amid her years-long recovery, “people took advantage of me.” “I had $18m saved because of all my success, but when I got back into my bank account, it was all.