Lil Wayne
Earlier this year, Wayne had to pay off a $1.13 million IRS tax lien for unpaid taxes stemming from 2004, 2005 and 2007. But his financial problems didn’t end there. Over the past two years, Wayne has been sued by producers Deezle, Jim Jonsin, Bangladesh and, most recently, rapper Rich Rick for failing to compensate them for beats or reportedly stealing beats.