Francis Ford Coppola
Francis Ford Coppola makes more wine than films nowadays, and that's likely because of his famous budget overages that ravaged his film sets. After he went into debt from Apocalypse Now, despite the movie's popularity, he dropped even further when his following movie, One From the Heart, flopped. Coppola declared bankruptcy in 1982, and several years later he opened one of the most successful wineries in human history.
Mark Twain
Although Twain appeared wealthy and had a wealthy spouse, his line of work wasn't lucrative enough for him to live comfortably. Twain's publishing company went bankrupt in 1894, and he was forced to declare bankruptcy. Slowly but surely, Twain recovered, but he then lost $30,000 from a shifty investment and died dirt poor.
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