Oh the irony. After making a film called The Debtors, starring himself and directed by his rather talent-deprived wife Evi, Quaid went broke. The decade ended with Randy Quaid banned from stage acting and the Quaids arrested for allegedly defrauding an innkeeper.
Shortly after her album Secrets went platinum with No. 1 hits "You're Makin' Me High" and "Un-Break My Heart," Braxton declared bankruptcy thanks to free-spending ways beyond her success. So much for learning her lesson, though - by 2010, the R&B singer was bust a second time. If that's not enough public embarrassment for you, tune into the sordid affairs and finances of Toni and her kin in the Braxton Family Values reality show on WE.
Despite the massive success of comic book heroes like Spider-Man, The Incredible Hulk and The X-Men, Stan Lee was a dot-com disaster. His web-based comic book venture of the era, the eponymous Stan Lee Media, quickly burned through its capital like so many other firms inflated by the tech bubble. Adding insult to injury was that Lee's partner, Peter Paul, was accused of securities fraud, too.
After legal troubles relating to sexual assault charges, the former boxing champ was bankrupted by lawyer fees -- and lavish spending on cars, mansions and Bengal tigers. This was before facial tattoos and ear biting, but no less embarrassing.
OK, OK, The Donald loves to split hairs over the fact that he personally hasn't gone bust. But the fact that Trump's Atlantic City hotel and resort company filed Chapter 11 bankruptcy twice this decade to reorganize debts related to construction still speaks a great deal.
Baseball star and (absurdly) investment guru Dykstra recently filed for Chapter 11 thanks to an ill-advised business venture -- a glossy magazine for millionaire athletes called The Players Club. Not only was Chapter 11 necessary, but the business resulted in 20 lawsuits. Another interesting rub is that from 2005-09, he was an investing columnist for TheStreet.com and endorsed by Mad Money star Jim Cramer ... except he was pumping up stocks for personal gain and got into trouble with the SEC. (Read more about "Nails" and others famous bonehead investors in an older column about investment failures of the stars.)
The youngest in the famous acting family, Stephen Baldwin has never quite made the same amount of money as his brothers. Unfortunately, that didn't stop his free-spending ways -- and reality show appearances weren't enough to offset his mortgage and other debts. Baldwin and his wife filed bankruptcy in New York in early 2009 and suffered foreclosure. At the time, he owed more than $2.3 million -- and his New York property was valued at only $1.1 million. Talk about underwater mortgages ...
Football star Michael Vick saw financial problems as a direct result of legal problems. The infamous dog-fighting ring cost Vick his endorsements and his NFL paycheck -- including a 2007 clawback by the Atlanta Falcons, where the team demanded that he reimburse them for $20 million of his $37 million bonus. As a result, Vick filed bankruptcy from behind bars in 2008.
The family-friendly comedian and '90s mainstay had his share of hits, but apparently didn't pay his share of the taxes. Thanks to disputes over income from Jingle All The Way and other movies, the state of California filed a lien for more than $2.5 million in unpaid taxes in 2008. Sinbad filed bankruptcy in December 2009. Ho ho ho!