Making a lot of money doesn't mean it will last. I guess some people just can't handle the big bucks when they are famous. Boxer Mike Tyson is one of the many.
Tyson had earned over $300 million during his career as a boxer but jewelry, mansions, cars, limousines, cellphones, parties, clothing, motorcycles and Siberian tigers eventually caught up to him. In 2003 he had to file for bankruptcy, thanks to a colourful variety of debts including $13.4 million to the IRS and a $9 million divorce settlement to his ex-wife, Monica Turner. From 1995 to 1997, he spent $9 million in legal fees, $230,000 on pagers and cellphones, and $410,000 on a birthday party. In June 2002, he owed $8,100 to care for his tigers and $65,000 for limos.
http://www.cosmoloan.com/loans/from-riches-to-rags-10-celebrities-who-went-broke.html
From the Upcoming ueue, submitted by Nightcrawlerx.
i met mc hammer once, and whenever i tell people that, they ask if he looked broke or something, but really he seemed fine. dressed well with a chain and all, in a nice hotel. really nice guy too, he took a picture of my family.