38. The Legendary Journey of Mickey Rooney
Joseph Yule Jr., better known as Mickey Rooney, charted an iconic path in entertainment. His nearly ninety-year career boasts over 300 films, making him a standout figure from the silent-film age to a revered character actor.

Despite earning top billing and significant earnings, Rooney’s life was marked by financial challenges due to a gambling addiction, leading to repeated bankruptcies. Remarkably, Rooney’s career didn’t falter; he performed until his death in 2014, leaving behind a legacy larger than his final estate of $18,000.