Dionne Warwick, singer
It is unclear how much Warwick has earned over more than five decades in the music industry, but it is known that she had more than 60 charted singles, global album sales totaling more than 100 million copies, two children’s books, a best-selling autobiography, and a fragrance line.
In March 2013, the legendary hit maker, 72, claimed in a federal court filing for bankruptcy that she owes $10.7 million, most of it for taxes.
Sinbad, comedian, actor
The comedian filed for bankruptcy for the second time in April 2013. Sinbad, real name David Adkins, first filed in 2009, but it was dismissed because he did not file the right documents, according to TMZ.
In the second go-round, Sinbad claimed he owed debts of about $11 million, $8 million of which stemmed from back taxes 1998-2006 and 2009-2012.
Sinbad showed little regret for his current financial situation, telling Oprah Winfrey last spring: “I didn’t buy Bentleys. I didn’t live large. I invested in me. I invested in a lot of other people. I would not change it; I would not go back.”

