5. From Rich to Broke
Though he was one of the hottest artists in the game at one point, T-Pain says he once went dead broke at one point and we mean broke. Pain says he went from having $40 million in the bank to $0 just like that. Things were so dire for him at that point that he “had to borrow money to buy my kids Burker King.” He credits bad spending and horrible real estate investments for his financial ruin. We’re sure buying all those top hats he was known for back in the day played some role in that too.