12 Of The Ugliest Celebrity Bankruptcies In History

mike tyson

There’s nothing quite like America’s obsession with celebrities …  unless, of course, you consider our obsession with celebrity failures.

After all, the shine of a rising star is always eclipsed by the blazing fire caused by a big bank account going up in smoke.

Some high-profile bankruptcy news of late includes:

  • A famous New York art gallery that has gone under, leaving the fate of a 500-year-old Botticelli painting up to the bankruptcy judge.
  • College football coach John L. Smith has a 132-86 lifetime record, and just landed a gig in the SEC leading up the Arkansas program. Too bad off the field, bonehead real estate moves have driven the Razorbacks coach to the brink of bankruptcy.
  • “Octomom”  Nadya Suleman has been foreclosed on in her latest bout with financial insolvency.

But these recent headlines are nothing compared with some of the ugliest celebrity bankruptcy stories in history.

Randy Quaid (Bankrupt in 2000)

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.

Vince and Linda McMahon (Bankrupt in 1976)

The brains behind World Wrestling Entertainment clearly didn't have a head for finance in the beginning.

The couple was in the hole $1 million as the wrestling empire started to blossom.

That included footing the bill for such crazy schemes as a failed Evel Knieval attempt to jump Snake River Canyon and a fight between Muhammad Ali and Japanese wrestler/martial arts star Antonio Inoki.

Oh yeah, and they didn't like the IRS too much -- racking up $142,763 in unpaid income taxes over five straight years.

Donald Trump (Business bankruptcies in 2004 and 2009)

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.

MC Hammer (Bankrupt in 1996)

Stanley Kirk Burrell, as the rap star was named at birth, is one of the best-known tales of celebrity excess.

After earning a reported $33 million in the calendar year 1991 alone he was saddled with debts worth $14 million at the time he filed for bankruptcy.

Those debts include race horses, 17 cars, an aeroplane, a record label and a home on nearly 12 acres that was bought for $30 million -- and offered for $6.8 million after the bankruptcy.

Oh yeah, and don't forget the $500,000 he owed to Deion Sanders according to filings. MC Hammer spent as much as $500,000 a month on a crew as large as 200 people, according to reports.

Nice work if you can get it! But don't fret, because in the intervening years Hammer has bounced back.

According to reports he is in the process of creating his own search engine, called WireDoo, which will compete with Google and Microsoft search engine Bing. I'm sure it will be a profitable business venture for him …

Stan Lee (Bankrupt in 2001)

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.

Toni Braxton (Bankrupt in 1998 and again in 2010)

Mike Tyson (Bankrupt in 2003)

Lenny Dykstra (Bankrupt in 2009)

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. (Read more on this in an older column about investment failures of the stars.)

Most recently, he was convicted of bankruptcy fraud -- facing up to 20 years in prison for hiding sports memorabilia and other items from liquidators and then selling it after the fact.

The icing on the cake? He previously pleaded no contest to grand theft auto and exposing himself to women he met through classifieds site Craigslist.

Michael Vick (Bankrupt in 2008)

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 claw-back by the Atlanta Falcons, where the team demanded that he reimburse them for $20 million of the $37 million bonus.

As a result, Vick filed bankruptcy from behind bars in 2008. He's starting to get back on his feet, but don't think this has anything to do with voluntary behaviour.

According to a stark 2010 report by ESPN, two-thirds of every dollar Vick earned in those first few years went directly to creditors and taxes. The rest is strictly controlled as more of an allowance for a child than true adult finances.

His creditors stand to receive $12 million through 2015, provided Vick continues to receive a multi-million dollar salary … but Vick himself isn't going to be piling up the cash anytime soon.

Burt Reynolds (Bankrupt in 1996)

If you think tabloid news about Tom Cruise and Katie Holmes breaking up is a recent phenomenon, just harken back to the high profile divorce of Burt and Loni Anderson.

The messy proceedings saddled him with $10 million in debt even as an extravagant lifestyle and a chain of failed Florida restaurants bled him dry.

The money troubles haven't stopped, however, as Merrill Lynch Credit recently has threatened to foreclosure on his four-acre waterfront estate in Florida to collect a $1.2 million debt.

And until recently, he owed California $225,000 in back taxes over about 15 years.

Anna Nicole Smith (Bankrupt in 1996)

A sexy Playboy playmate in her late 20s, Anna Nicole sidled up to the elderly but filthy rich J. Howard Marshall, who made a fortune of $1.6 billion in the oil industry.

They were wed and after 14 months, Marshall died. Smith expected to inherit a bundle … but the courts decided she would get nothing.

The result of a $400 million budget going to zero was mighty painful, and resulted in bankruptcy.

Adding to the troubles was that a former female maid sued her for sexual harassment and the resulting $850,000 fine was tacked on.

Anna Nicole led a troubled life after that, including drug abuse and death under odd circumstances in 2006.

Lawrence Taylor (Bankrupt in 2009)

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