Lil’ Kim

Rapper Lil Kim reportedly spent much of her fortune undergoing various types of plastic surgery. After spending time in jail Lil Kim has not been able to kick start her rap career again. In fact, in 2008, Background Media (her former record label) sued her for an amount of $2.5 million and prevented her from being able to release any albums. In 2012 it was reported that Lil Kim owed $1 million for seven years’ worth of taxes she hadn’t paid.

Fat Joe

Fat Joe is another rapper that has found himself broke. The rapper served a four month prison sentence for failing to pay $700,000 worth of taxes between 2007 and 2008. He blamed his lack of tax payments on those he had authorized to manage his money.