2: Michael Jackson

Source: Billboard

Even the King of Pop and the best-selling artist of the 21st century, Michael Jackson was not insured against tax man’s troubles. Apart from making amazing record-selling albums, the millennium artist also made headlines for his extravagant lifestyle. He had a track record of spending money on most outrageous things including a private amusement park, petting zoo and exotic animals at his $14.6 million residence Neverland ranch.

But as they say, all good things come to an end. His downturn eventually started when he was sued for a child abuse civil lawsuit and had to settle the case for $22 m. In 2006, he had to refinance the $200 million loan he secured from Bank of America to stave off bankruptcy. By 2009, Michael Jackson was neck deep in debt and was estimated to be owing closed to and at the time of death, he was estimated to owe close to $ 400- 500 million in loans and mortgages.