Rapper Curtis James Jackson III, better known as 50 cent, has filed for chapter 11 bankruptcy protection, reports the Wall Street Journal.

The rapper’s bankruptcy filing came on the heels of a jury verdict in a lawsuit with Lastonia Leviston, for which the rapper was ordered to pay Leviston $5 million for intentionally leaking a sex tape of her.

The former drug dealer-turned-musician, whose claim to fame was his 2003 platinum album Get Rich or Die Tryin’, has since become a bona fide businessman. Over the past few years, he’s invested his greenbacks in a variety of projects including a headphone company, record company, vodka brand, and his most lucrative venture to date, Vitamin Water.

Photo: Spencer Lowell.

As a minority shareholder, the rapper raked in a reported $100 million when the company was sold to Coca-Cola in 2007, and his net worth was valued at $155 million in May. Just days ago, the New York Times did a profile of the entrepreneur, describing him as having “exceptional business instincts.”

But where else did the native New Yorker park his money? Well, in an expensive car collection. According to Forbes, the rapper has quite the flashy stockpile, which boasts a Rolls-Royce Phantom, two Chevrolet Suburbans, that have bombproof undercarriages, a cobalt blue Lamborghini Murielago, a Ferrari convertible, a Bentley Mulsanne, and a Yamaha YZR-R1 motorcycle. Jackson also seems to have a fascination with the color blue.

artnet News reported that cars have overtaken art as an investment class, but that mostly pertains to vintage collectibles, we’re guessing the tricked out bulletproof Suburbans won’t be hitting any auction block soon.

Photo: Spencer Lowell.