In the 1980s and 1990s, mega popular singer MC Hammer made a huge fortune. And then he spent a lot of it on a huge mansion... not to mention a wardrobe full of "Hammer pants." Hammertime came to an end in 1996 when the rap star filed for bankruptcy.<a href="http://www.divinecaroline.com/112939/116797-mo-money-mo-problems-eight/…; target="_blank">Source.</a>

Michael Jackson's Neverland Ranch sure cost him a pretty penny. The King of Pop reportedly spent $35 million improving the property which included several amusement park rides, two railways, a fire department, and of course a zoo. MJ also owned 75 cars and famously bought Elizabeth Taylor a $637,000 necklace. Upon his death, Jackson was reportedly in $400 million worth of debt.<a href="http://www.cosmoloan.com/loans/from-riches-to-rags-10-celebrities-who-w…; target="_blank">Source.</a>

In 2003, Mike Tyson, who was once worth over $300 million, filed for bankruptcy. Iron Mike spent his fortune on mansions, Bentleys, jewelry... and tigers. The Hangover anyone? Despite his financial woes, Tyson said, “I’m totally destitute and broke. But I have an awesome life, I have an awesome wife who cares about me…I had a lot of fun. It [losing all his money] just happened. I’m  very grateful. I don’t deserve the wife I have, I don’t deserve to have the kids I have, but I do, and I’m very grateful.” Positive outlook guy!<a href="http://www.dailyfinance.com/2012/02/15/broke-stars-11-celebrities-who-w…; target="_blank">Source.</a>

In 1999, Randy Quaid was in a film called The Debtors. The next year, Quaid was just that, in debt. Isn't it ironic? Dontcha think? Randy filed for bankruptcy in 2000 and was arrested for allegedly swindling an innkeeper.<a href="http://investorplace.com/2012/02/10-most-embarrassing-celebrity-bankrup…; target="_blank">Source.</a>

Sinbad, the comedian not the <a href="http://en.wikipedia.org/wiki/Sinbad_the_Sailor" target="_blank">sailor</a>, declared bankruptcy in 2009 after defaulting on his taxes. In court, Sinbad claimed he had $50,000 in assets and $10-$50 million in liabilities. That's a big deficit. <a href="http://www.luxurylaunches.com/celebrities/celebrities_gone_bankrupt_in_…; target="_blank">Source.</a>

Things got real for Real Housewife of New York City, Sonja Morgan, in 2010 when she filed for bankruptcy with $19.8 million in debt and only $13.5 million in assets. Only $13.5 mil... poor gal.<a href="http://www.nydailynews.com/news/money/bankrupt-celebs-gallery-1.2915?pm…; target="_blank">Source.</a>

Stephen Baldwin, the youngest brother in the famous acting dynasty, was forced into bankruptcy due to his free-spending ways in 2009. Maybe Jack Donaghy can give him some advice?<a href="http://investorplace.com/2012/02/10-most-embarrassing-celebrity-bankrup…; target="_blank">Source.</a>

Donald Trump has filed for bankruptcy twice! Ok it was his casino, but still. The Donald claimed losses of around $1 billion when his casino went under in 1992 and 2004.<a href="http://www.nydailynews.com/news/money/bankrupt-celebs-gallery-1.2915?pm…; target="_blank">Source.</a>

After Toni Braxton's album Secrets went platinum, she spent her way into bankruptcy, and had to file twice in 1993 and 2010. The No. 1 hit Un-Break My Heart should be called Un-Break My Bank.<a href="http://investorplace.com/2012/02/10-most-embarrassing-celebrity-bankrup…; target="_blank">Source.</a>Check out a sneak peek for the SO new show My Shopping Addiciton premiering on October 15 at 11/10C <a href="http://features.oxygen.com/videos/My%20Shopping%20Addiction/Season%201/…;