Once thought to be capable of rivaling Kanye West in album sales less than a decade ago, Curtis "50 Cent" Jackson filed for chapter 11 bankruptcy on Monday, Wall Street Journal reports.

According to the Journal, Mr. Jackson "reported assets and debts each in the range of $10 million to $50 million." The announcement of bankruptcy comes one day after reports emerged of Jackson needing to pay $5 million to a woman whose sex tape he acquired and then uploaded to the internet after adding his own commentary.

It's somewhat of a nadir for 50, whose musical career peaked in the mid-2000s with his first two albums, Get Rich Or Die Tryin' and The Massacre. To simply call that a peak, though, understates the scope and influence of 50's presence in that period of time—at one point, the guy had three singles in the Billboard's top five in the same week, the first artist to ever pull that off.

After his music career cooled off in the late-2000s, 50 remained relevant (and ostensibly wealthy) with a wise investment in Vitamin Water, netting him around $60 million to $100 million and putting his net worth around $500 million in 2010. (He also started acting; he's currently on the Starz series Power and has a role in the forthcoming Jake Gyllenhaal boxing film Southpaw.)

Though he'd gone a bit without putting out a hit record—50 told GQ after his 2009 record Before I Self Destruct flopped that "maybe (he) was supposed to be under a palm tree, instead of putting the record out"—there weren't many signs he was in financial distress, perhaps save for the announcement on Friday that he'd be signing vodka bottles at a suburban Wisconsin grocery store. In 2009, he said that he'd lost "a few million" in the recession, but last year Forbes put his net worth at $140 million.

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Michael Rosen is a reporter for Fusion based out of Oakland.