Wayne Newton
Wayne Newton was huge in the '60s, but he was ultimately unable to sustain his fame. By 1992, Newton was bankrupt and $20 million in the hole. The IRS sued him in 2005 for failing to pay the $1.8 million he owed them on his home, which was eventually seized in 2010. Today, all of Newton's assets have been liquidated, and he has been unable to recover.
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