#23: Struggled with Financial Woes

Despite earning millions during his peak, Reynolds’ lavish spending, bad investments, and costly divorce settlements left him in serious financial trouble. By 1996, he was forced to file for bankruptcy, owing over $10 million.

His financial troubles were widely publicized, and he had to sell off his beloved Florida ranch. Though he continued to work steadily, many later roles were low-budget films or guest TV appearances. Despite these hardships, Reynolds always maintained a sense of humor about his misfortune, joking that he had been “rich and poor more than once.”