3. Toni Braxton: The ravishing R&B star, a six-time Grammy winner who’s sole more than 40 million albums, has declared bankruptcy twice, both in 1998 and 2010. 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.
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