Sometimes poor money management can be the downfall of a star, even one as successful as pop music icon Billy Joel. His ex brother-in-law’s risky business moves as his manager caused Joel to file for bankruptcy. Joel eventually filed a $90 million lawsuit against his former relative, hoping to restore some of the funds he lost.

Another star guilty of living too large, Cage has owned as many as 15 homes at once, more than twenty cars, and millions of dollars of art and jewelry. His former manager reported that Cage’s lifestyle costs around $30 million a year. It was reported in 2009 that he’d fallen $6 million behind in his taxes and had filed a $20 million lawsuit against his money manager

Even though she could be seen each week shaking it on Dancing With the Stars last year, Anderson was dealing with some serious IRS issues behind the scenes. She joined the delinquent taxpayers list after failing to pay $493,000 in personal income tax. Anderson blamed the situation on the recession but says that it’s since been straightened out. She told the The Daily Mirror in 2010: “Everyone went through a lot in the last couple of years. The economic situation caused a lot of stress. People didn’t pay me, but it’s all sorted out now.”

When the teen soap The OC premiered in 2003, the future looked bright for Barton, one of the show’s most promising young stars. Since then, she’s faced personal issues, as well as failed TV and movie roles, and she’s paying for it. Barton was sued in 2010 for not paying rent on her New York City apartment. This year, TMZ reported that she was ordered by a judge to pay $95,000 to a private nursing company for services rendered in 2009.

After Stewart was indicted in 2003 for insider trading, the queen of domesticity was sentenced to five months in jail—a period that she estimated cost her empire of magazine, TV and lifestyle products $1 billion. Recent reports indicate that the company is now considering partnership options, or even a potential sale, after its market value dropped to $551 million this year from a peak of $1.9 billion in 2005.

The Wayne’s World star found herself in hot water early in her career when, in an attempt to get out of a contract with General Hospital and join the A-Team, she filed a lawsuit against ABC. Carrere lost the suit, and was forced to declare bankruptcy at just 19. She’s made wiser money decisions in recent years, signing a prenup with her ex-husband that protected most of her assets in their 2010 divorce.

Love’s struggled for years with substance abuse problems and custody battles—and money troubles seem to follow her through it all. After her husband Kurt Cobain’s 1994 suicide, she inherited much of his valuable estate. But due to her own money issues, Love had to sell her share of the Nirvana recordings for an estimated $50 million in 2006. She continues to face endless lawsuits for failing to pay employees and defaming people on Twitter, including her former lawyers.

This Oscar nominee—for Goodfellas—was forced to file for bankruptcy because of extensive legal fees from a custody battle with former boyfriend Harvey Keitel, leaving her broke. She’s been able to pay back almost $2 million of her debt with real estate investments and a lucrative role on The Sopranos.

Related: Stars Who Went from Rags to Riches

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