Basinger nailed star-making roles in the 80s alongside Sean Connery and Robert Redford in the Bond film Never Say Never Again and The Natural. But by the end of the decade she found herself in financial trouble when her investment group purchased a town in Georgia for $20 million. Then, in 1993, Basinger was sued for pulling out of a film, forcing her to declare bankruptcy and sell the town. But better times were ahead: she later had the decision reversed and found even greater success on-screen, winning the Academy Award for her role in 1997’s LA Confidential.
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.
Six-time Grammy-Award-winner Braxton has had her share of money troubles through the years. The R&B songstress filed for bankruptcy in 1998 when she couldn’t pay back her record company for production and promotion costs. And last year Braxton filed for a second time after health issues caused her to cancel her Las Vegas show, a deal she had brokered with her own money. There was even a chance that she might lose her Grammys if her property was seized and sold. But it looks like Braxton may be able to keep her belongings after all: A court ruling relieved her of personal liability for certain debts and barred debtors from trying to collect.
Bernie Madoff’s $65 billion Ponzi scheme victimized thousands of people, and this Hollywood couple was among the hardest hit. They lost an unknown, significant sum through investing with the corrupt money manager. But Bacon says they weren’t defeated, telling Details: "I'm not going to say it didn't have its emotional downsides. But we're both young, and we both had the ability to work and roll up our sleeves and start putting the pieces back together. The truth is that we went through it together
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.”
Though his older brother Alec enjoys the fruits of his labors as a successful film and TV actor, Stephen Baldwin’s earnings as a reality show star and spokesperson never seemto catch up with his spending habits. In 2009, his $2 million debt landed him in bankruptcy. But that hasn’t scared him away from the courts: Last December he filed a $3.8 million lawsuit against Kevin Costner for “duping” him into investing in Costner’s oil-separating technology.
The former boxer—and ear connoisseur—says he now lives paycheck to paycheck following years of excessive spending and an unruly lifestyle that led to many alcohol- and drug-related arrests. He filed for bankruptcy in 2003, but has since made an attempt to turn his career around, landing a scene-stealing role in The Hangover and a reality show. He said on The View: “I’m totally destitute and broke. But I have an awesome life, I have an awesome wife who cares about me.”
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.
Snipes’ successful career as an action star was brought to a screeching halt when he was sentenced to federal prison for three years in 2010 for failing to file his taxes. He was convicted in 2008, but spent two years appealing the sentence before surrendering to the state, and he continues to fight for an appeal from behind bars.
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.
He soared through the 70s as one of the biggest movie stars of the time, but Reynolds’ lavish lifestyle of expensive homes and costly divorces caught up with him years later. In 1996, he owed $10 million to his creditors and filed for Chapter 11, but Reynolds lucked out: He got to keep his luxurious estate and emerged from bankruptcy in 1998.
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.