No.3: Burt Reynolds
Once dubbed “the sexiest man alive,” Burt Reynolds was a Hollywood golden boy in the 1970s. But by the early ’90s, the shine had faded. Film roles dwindled, and his 1993 divorce from actress Loni Anderson saddled him with steep alimony payments.
In 1994, after losing his Florida mansion and with mounting debts, Reynolds declared bankruptcy. His downfall shocked fans, but he didn’t disappear. His role in Boogie Nights (1997) earned him an Oscar nomination and helped revive his career—making him a symbol of both Hollywood glamour and grit.
No.2: Donald Trump
Before his presidency, Donald Trump was known for flashy deals and big risks. Though he never declared personal bankruptcy, four of his companies—including casinos and hotels—filed for Chapter 11 between 1991 and 2009.
In the first case alone, Trump was personally liable for $832 million and even had to sell his yacht, The Trump Princess. Still, he used legal loopholes to shield his personal wealth, recover, and continue amassing billions. His bold tactics earned him celebrity status—and eventually the presidency.
