10 Celebrities Who Lost Big Financially

Kevin Bacon and Kyra Sedgwick

Sure, everyone knows now not to invest with Bernie Madoff, but someone should have told Mr. Six Degrees and his wife The Closer that before Madoff uncorked his $50 billion Ponzi scheme on them and the rest of the investing world.

The pair reportedly lost millions of their personal investments in the scheme and, while it may have been somewhat comforting to know that Hollywood figures such as Steven Spielberg and Jeffrey Katzenberg were duped in the same deal, it had to be humbling for the already prolific Bacon to tell Life & Style magazine in 2009 that "I need to work, for obvious reasons." Remember this when you're inundated with commercials for any of Bacon's four projects slated to hit the screen this year.

Wesley Snipes

During tax season, we at the TheStreet would like to remind that even if you're suddenly adding millions of dollars to your paycheck, you need to file a tax return every year. The star of the Blade movies got no such advice when he made more than $38 million since 1999, but only started filing tax returns in 2006. We still don't quite understand this.

Snipes paid taxes on his earnings from Wildcats, Major League, White Men Can't Jump, Jungle Fever, Mo' Better Blues, Passenger 57 and Rising Sun, but suddenly he starts playing a samurai vampire (sorry, daywalker) and he's invulnerable to taxes? Did those eight straight-to-DVD movies he's made since 2004 weaken his powers?

Don't worry, Snipes has plenty of time to ponder this after his final appeal failed last year and he started his three-year prison sentence in December.

Madonna

Ordinarily a fairly savvy businesswoman -- especially considering she started her Maverick record label with Time Warner (Stock Quote: TWX) almost 20 years ago before that was a thing to do -- Madonna's one major blunder came during her marriage to Guy Ritchie, which was filled with them.

Forget her and Ritchie's heavy ordnance of a film Swept Away, her "British" children's book The English Roses, her directorial debut Filth and Wisdom, her American Life album and her affected English accent -- you marry a guy who directs heist movies like Lock, Stock and Two Smoking Barrels and Snatch for a living and you don't sign a prenuptial agreement?

Madonna was worth $500 million during her marriage to Ritchie and, while the director didn't clean her out when their marriage dissolved in 2008, the $75 million he reportedly got was a nice parting gift.