16: Wesley Snipes
At one point in time, Wesley Snipes was one of the highest paid performers in Hollywood, because of the Blade trilogy which game a boost in his career. He was a well-known figure and high earner—about $40 million from 1999 to 2004—that not paying taxes was hard to fathom. Snipes followed an accountant and an anti-tax advocate down a dangerous path. The advisers claimed that he does not have to pay the taxes legally.
He owed the IRS Department a whopping amount of $12 million mortgage payments in taxes! This finally ended up with Snipe being served a 3-year jail sentence. Now that he is out, it could be probably expected that he has a financial advisor to guide him through his finances.