#14: Francis Ford Coppola
After directing The Godfather and Apocalypse Now, Francis Ford Coppola was one of the most powerful filmmakers in Hollywood. In 1980, he bought his own movie studio. Then he bet big on his next film, a musical called One from the Heart. It was a risky move.

The movie cost about $26 million and was a huge flop, earning back only a tiny fraction of that. His studio collapsed under the debt, and he filed for bankruptcy more than once. Coppola recovered by directing hits like Dracula and by building a hugely successful wine business.
