Stephen Baldwin
Baldwin was forced to file bankruptcy by the IRS in 2009. He was behind on taxes, mortgages, credit card payments, and personal debts that he couldn't even dream of paying back. Baldwin's house was forclosed in 2017, and he was arrested shortly afterward for failing to pay taxes. He served five years in prison and is still working on paying back the money he owes.
Anna Nicole Smith
Anna Nicole Smith was able to flip her modeling career into a reality tv career, which eventually flipped against her. She married 86-year-old billionaire J. Howard Marshall just three months before he died, and he ended up leaving her nothing. She filed bankruptcy after a sexual harassment case against her won a former employee her last $800,000.
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