Sex, drugs and tax evasion? Getting in trouble for taxes is probably one of the least sensational crimes a celebrity can commit, yet their are countless celebrities who have gotten themselves into trouble for avoiding these payments.

In 1999 Wesley Snipes stopped paying his taxes and started keeping his money in offshore accounts through 2004, as per the advice of individuals Snipes referred to as “professionals.” Snipes, now imprisoned as of Dec. 9, is serving a three year sentence for tax evasion charges that totaled a staggering $13 million sum. Not only has Mr. Snipes’ last seven films gone directly to video – with the exception of Brooklyn’s Finest (which received a 43% rating on RottenTomatoes.com) – he will live the next three years in prison confinement. Why? Because Wesley felt he was above the law, exempt from the civic dues every hardworking American citizen must realize. The news here is not how Wesley could forfeit his freedom to save a fraction of his multi-million dollar fortune but that even celebrities, who are very well off, can be incredibly stupid.

Most baffling, though, is how millionaire celebrities can and will forfeit their possessions and freedom by avoiding the IRS.
In Need of a Helping Fan

The IRS, for example, caught up with country artist Willie Nelson in the early nineties for over $16 million of unpaid taxes. Mr. Nelson then auctioned his possessions and performed benefit shows to meet his debt obligations. Snipes, however, fought the allegations and even went so far as to claim that he was “a nonresident alien” of the United States.

It’s Willie Nelson who made the best of his tax negligence, totaling $16 million, for the IRS sold off his personal assets which his fans then purchased and gave back to him. Willie, also, recorded an album, titled The IRS Tapes: Who’ll Buy my Memories?, and played benefit concerts that ultimately paid off his back taxes.

Sometimes it takes a tussle with the law to set an absent minded celebrity straight — straight enough to hire a new tax accountant. Sometimes, though, it results in jail time, a much steeper price to pay than a federal income tax percentage.
Other Trouble Makers

Famed photographer Anne Lebowitz dominated headlines for a short while in 2009 when it came to light that she had to borrow money to pay off outstanding debt, totaling $15 million. She owes the IRS over $2 million, including $275 K in state liens.

Nicolas Cage is just as well known for his roles in Hollywood feature films as his is for his reckless spending. Mr. Cage now has a mountain of debt and at one point owed the IRS over $6.5 million.

Randy Quaid has been on a steady decline since Independence Day. Mr. Quaid reportedly owes over$1 million in back taxes.

Celebrities live inside an alternate reality where money is a non-concern but at some point, their debt accumulates to an unmanageable amount. This is when the IRS gets involved; and then we get to read about it!