No.5: Francis Ford Coppola

Despite directing The Godfather trilogy, Francis Ford Coppola faced severe financial woes. The failure of his 1982 musical One from the Heart—which cost $27 million but made only $4 million—dealt a heavy blow.
Coppola filed for bankruptcy three times: in 1982, again in 1990, and once more in 1992. At one point, he had $98 million in debt and $52 million in assets. Yet he never gave up filmmaking. He bounced back by producing new works and launching successful ventures in winemaking and boutique hospitality.
No.4: Larry King

Before becoming a TV icon, Larry King hit rock bottom in the early 1970s. While working as a Miami radio DJ, a scandal cost him his job and income, and he sank into $352,000 of debt.
In 1978, King filed for bankruptcy and considered giving up. But fate intervened when he was offered a late-night radio show in Washington, D.C.—which eventually evolved into Larry King Live on CNN. He went on to become one of America’s most beloved talk show hosts for over two decades.