If you have an entourage of 200 people that costs half a million dollars every month, but no Scrooge McDuck-type swimming pool filled with gold, chances are you'll probably go bankrupt. And that's precisely what happened to MC Hammer.

The 'U Can't Touch This' rapper has some of the most well-known financial problems in the music business to date. In 1990, the rapper's album 'Please Hammer, Don't Hurt 'Em,' net profits of $33 million! He and his over-sized entourage were riding the gravy train... or so he thought.

The '2 Legit 2 Quit,' rapper filed for bankruptcy in 1996, as he was $13 million in debt with only $9 million to his name.... bit of a disconnect there.

Hammer's cash flow issues have not been totally resolved, however. As recently as 2011, Hammer still owed the IRS almost $800,000 in back taxes from his earnings in the '90s. Might we suggest a high-quality line of Hammer pants to pay off your debts?

Looking back, a more appropriate hook to his hit 'U Can't Touch This' would have been, "Stop! Fiscal responsibilty time!" There's not much of a ring to it, but teaching good spending habits is important, as Hammer knows all too well.

Watch MC Hammer Talk Bankruptcy on 'The Opie & Anthony Show'