Burt Reynolds
"I've lost more money than is possible because I just haven't watched it," said Reynolds in a 2015 Vanity Fair interview. Reynolds went on an unchecked spending spree that lasted nearly 20 years, but everything caught up to him in 1996 when he had to file for bankruptcy. But, when Boogie Nights came out just one year later, Reynolds was able to make his money back and then some.
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