5. Willie Nelson: The On The Road Again singer was deep in debt to the taxman in 1990, claiming in court papers that he owed the IRS more than $16.7 million when filing for bankruptcy that year. 7. LaToya Jackson: The quirky bombshell of the Jackson clan, who’s appeared in Playboy, could not replicate her brother Michael’s success on the charts, leading her to declare bankruptcy in 1995 after amassing a mountain of debt connected to her ill-fated singing career.
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