No.1: Michael Jackson
Despite being one of the most successful entertainers of all time, Michael Jackson’s finances were in shambles by the 2000s. His accountants warned that he was “on the brink of bankruptcy,” with $70 million in bank loans and monthly expenses exceeding $2 million.
Jackson continued spending extravagantly on luxury goods and real estate. When he passed away in 2009 at age 50, his debts totaled over $500 million. Though his estate eventually paid it off through music royalties and licensing deals, his story is a cautionary tale—even legends aren’t immune to financial ruin.
