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. 9. Larry King: Prior to a career-defining 25-year-run on CNN, the retired talk show icon had his share of financial worries, filing for bankruptcy in 1978 after he was unable to make good on more than $350,000 in debt.
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