5. Bill Cosby
Bill Cosby has been hitting some very hard times lately, as it seems every week another woman comes forward to accuse him of some sexual impropriety. His show has been pulled from syndication as audiences feel uncomfortable with his presence and he has more or less become a social pariah. Now 78, Cosby hasn’t done much performing in past decade, but that hasn’t stopped him from comfortably sitting on nearly $390 million. While many speculate due to failing health, he might not live to see the end of his legal battles, there is still a chance his estate might be culpable to pay out some punitive damages.
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