Few rappers have made their wealth more central to their fame than 50 Cent, which makes it rather uncomfortable for him that he filed for Chapter 11 bankruptcy in a Connecticut court today. His declaration comes just days after the rapper was ordered to pay $5 million to Rick Ross’ ex-girlfriend for distributing a sex tape involving her in 2009.

According to the document filed by his attorney, 50 lists between one and 49 creditors, with both assets and debts in the range of $10 million to $50 million.

Born Curtis Jackson, 50 was briefly the most popular rapper in the world, selling over 20 million copies of his first two albums between 2003 and 2005. He’s perhaps even more well-known for allegedly making hundreds of millions of dollarswhen Vitamin Water was bought by Coca-Cola. On his 2007 single “I Get Money”—his last good song, or at least his last important one—he rapped, “I took quarter water sold it in bottles for 2 bucks / Coca-Cola came and bought it for billions, what the fuck?”

It’s still unclear how, or to what extent, 50 Cent squandered his wealth, but the newly and suddenly rich spiraling into destitution is not a new story.