Curtis James Jackson III, the rapper better known as 50 Cent, filed for bankruptcy on Monday.
Documents filed in Connecticut Bankruptcy Court showed Jackson's total assets were listed in the range of $10 million to $50 million. He listed total liabilities in the exact same range.
The chapter 11 bankruptcy filing comes days after a jury ruled that Jackson must pay $5 million to a woman suing over a sex tape that was posted without her permission, according to the Associated Press. (Tweet This)
"This filing for personal bankruptcy protection permits Mr. Jackson to continue his involvement with various business interests and continue his work as an entertainer, while he pursues an orderly reorganization of his financial affairs," Jackson's attorneys said in a statement.
The bankruptcy may come as a shock to some considering Jackson's savvy business ventures and his status as one of hip-hop's wealthiest artists. Forbes has pegged his net worth in past at up to $155 million.
A sale of the rapper's stake in VitaminWater netted him about $100 million after taxes when Coca-Cola purchased the beverage brand in 2007.
After a sense of frustration with Beats Electronics, the headphones company co-founded by Dr. Dre and later bought by Apple, 50 Cent founded his own competitor SMS Audio in 2011. When Jackson appeared on QVC in 2012 the company sold more than $175,000 worth of headphones in nine minutes.
In a more recent venture, Jackson closed a $78 million deal at the end of 2014 with FRIGO Revolution Wear to promote men's underwear.
Read More 50 Cent signs $78M underwear deal
But filing for bankruptcy doesn't necessarily mean the Grammy award-winning rapper is out of money, according to Leon Bayer, bankruptcy attorney at Bayer Wishman & Leotta.
"Chapter 11 is the drug of choice for celebrity debt problems," he said. "You don't have to be broke to file for chapter 11, but it could mean you don't have good cash flow."
Whether or not that is the case will be made more clear sometime in the 14 days Jackson has to file his debt payment plan or "schedules," which could reveal intimate financial details.
"When he files schedules it's going to show all the details of his debts, assets, even whether or not he paid his gardener on time," Bayer said.
Intentionally or not, Jackson's bankruptcy will also put a roadblock between the $5 million he was ordered to pay and the woman winning her sex tape case was set to receive.
"It tells them they aren't going to get a check anytime soon, so why not sit back down at the negotiating table," he said.
Jackson's spending and business activity—including any salary drawn for himself—could be subject to the scrutiny and approval of bankruptcy court pending the review of Jackson's filing.