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12 Celebrities And Their Biggest Money Mistakes

There are few times in normal conversation in which the word "schadenfreude" can be thrown around. It means taking pleasure in the misfortune of another. For example, when the guy who cuts you off in

There are few times in normal conversation in which the word "schadenfreude" can be thrown around. It means taking pleasure in the misfortune of another. For example, when the guy who cuts you off in traffic ends up with his beamer wrapped around a street lamp, and you think to yourself "ha, serves him right" that's an example of schadenfreude. Chuckling at a high school bully who ends up unemployed, living in his mother's basement into his forties is another example.

One of the greatest examples of an event during which many people feel this complex emotion is when a widely disliked celebrity goes broke. Whether a bad actor or a repulsive singer, watching a famous person become miserable recalling their car being repo'd or their house taken by the bank, it sometimes feels good. While she isn't completely broke, Jessica Simpson recently indicated that marrying Nick Lachey was among the worst financial decisions she has ever made.

In reality however, there are tons of celebrities who have made vastly worse decisions with money. Jessica Simpson is still loaded and we estimate her net worth at around $150 million. Not too shabby for someone who considers a former marriage to have been her worst professional choice. With that said, whether it be a poor marital decision, a stupid career choice, an addiction or even poor spending habits, here is our list of twelve formerly-successful celebrities and their worst financial blunders. While you might feel sorry for some of these beloved stars, there are a few that are worthy of more than a few chuckles.

12 Toni Braxton: Terrible Overall Financial Knowledge

We start our list off with one of the most successful R&B singers of the past couple of decades. Toni Braxton has found success in four decades (1980's to present) but just can't seem to handle a buck. She is notorious for living well above her means and has declared bankruptcy multiple times.

11 Wesley Snipes: Taxes

10 Heath Ledger: Will Not Up to Date

9 Charles Barkley: Gambling

Oscar Wilde said it: "moderation in all things, including moderation". Basketball star Charles Barkley, never got the memo saying "gambling in moderation". Some forms of gambling are relatively harmless. A few dollars here or there on a baseball game or a fantasy football pool will never hurt someone, but betting the house, spouse or kids on whether or not team X will beat the spread is wherein lies the problem.

8 Willie Nelson: Taxes

Legendary country singer Willie Nelson is no fan of the man, man. He never made a secret about it and continues to be an anti-authoritarian figure to this day. Back in the early 90's, the IRS took nearly everything he had after he was discovered to have not paid taxes or severely underpaid for many years. He ultimately paid all of his debts off in the next couple of years, and sued his former money managers for keeping his money in illegal types of accounts, which was partially what he got in trouble with in the first place.

7 MC Hammer: Spending

MC Hammer may have sang a song about not being able to be touched, but his debtors pretty much had their way with him. He went completely broke because he didn't keep track of how much was coming in and how much was coming out. He dropped $30 million very quickly. His purchases and expenses were obscenely frivolous.

6 Mike Tyson: Spending/Taxes

Long before Floyd Mayweather, whose spending habits can be summed up in a quick visit to his Instagram page, Mike Tyson was the king of the boxing world. Much like "Money" Mayweather, "Iron" Mike could throw money around like none other.

5 Larry King: Scammed/Divorces

Larry King is a sharp man. In his years as a television host he has risen to the top of the media world, but his financial status has never been particularly rosy. Back in 2010 he filed for divorce for the eighth time (from his seventh wife), but did not follow through with the proceedings. Number seven, Shawn Southwick, has been in his life since 1997, his longest lasting marriage. Several of his other exes receive alimony payments in amounts that some co-workers have joked keep him tied to working at CNN because he needs the job.

4 Mel Gibson: No Pre-Nup

3 Gary Coleman: No Involvement In His Own Finances

2 Tiger Woods: Cheating

1 Michael Jackson: SPENDING

The fact that a few of the entries on this list included "spending" as a terrible mistake proves one thing, not watching how you spend is the worst financial mistake one can make. Even if your marriage goes well, your career stays fruitful and you don't get sued, throwing around more money than shows up every month will destroy anyone. Michael Jackson is no exception. When he was swimming in bills, he bought Neverland Ranch, which cost him nearly $20 million. The problem was however, he also had to maintain that. When your home has a zoo and a theme park, the costs can run up $10 million a year by some estimates. Furthermore, Jackson had expensive tastes and loved to spend, routinely dropping millions during shopping sprees.

Sources:  forbes.com, people.com, azcentral.com, cbsnews.com, dailymail.co.uk

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12 Celebrities And Their Biggest Money Mistakes