Wayne Newton had to file for Chapter 11 in 1992. He was $20 million in debt and had a lien of more than $300,000 with the IRS. The Las Vegas singer recovered, but has been in and out of court over money issues ever since.
LAS VEGAS, NV - OCTOBER 18: Entertainment Wayne Newton attends a Republican presidential debate airing on CNN, October 18, 2011 in Las Vegas, Nevada. Seven GOP contenders are taking part in the debate, which is sponsored by the Western Republican Leadership Conference in Las Vegas and held in The Venetian Hotel's Sands Expo and Convention Center. (Photo by Ethan Miller/Getty Images)