Last month, Michael Sorrentino — better known as “The Situation” from MTV’s Jersey Shore — was indicted (alongside his brother Marc Sorrentino) for allegedly failing to pay taxes on nearly $9 million of income. Thursday, Oct. 23., the brothers head to court for their arraignment in Newark, N.J. (Please note: the original arraignment was set for Oct. 6, but the judge kindly postponed it so The Situation could go film a reality show called Marriage Boot Camp in Los Angeles. No, we’re not making that up.)
The Situation and his brother face one count of conspiracy to defraud the United States, along with three and two counts, respectively, of filing false tax returns for 2010 through 2012. The Situation also faces an additional count for allegedly failing to file a tax return for 2011.
But Mr. Sorrentino is hardly the first celebrity to get into an, er, situation with the IRS. Here, a look back at some other stars who found themselves facing serious tax troubles:
What was it that finally brought down America’s most powerful mobster — who in this case we’ll consider a celebrity? Tax troubles. In 1931, authorities found Capone guilty of tax evasion and hit him with an 11-year sentence. By the time he was released, Prohibition was no more — and other mobsters had taken over his organization, as TIME reported. His health began to deteriorate too — a result of having contracted syphilis — and it was really just all downhill from there.
In 2013, the legendary hip hop artist served a three-month prison sentence after pleading guilty to tax evasion. The Grammy winner was convicted for failing to pay nearly $1 million taxes, People reported. She told the judge she intended to pay the taxes eventually, but was unable to do so during the period of time when she dropped out of the music business. Shortly before her sentence began, Hill took to her Tumblr to post a sprawling open letter, where she connected America’s deep history of racism to her IRS troubles.
When somebody mentions the name Willie Nelson, a few things probably come to mind: a twangy voice, long gray braids, a deep love for marijuana — and a hellish battle with the IRS. In 1990, the country legend owed $16.7 in unpaid back taxes and had to hand over many of his possessions to keep himself out of prison. To help pay his debt, the country crooner even released an album called The IRS Tapes: Who’ll Buy My Memories? in 1992. Nelson struck an agreement with the government that if the album sold 4 million copies, his debts would be cleared. That did not happen — but it did come close, pulling in $3.6 million. By 1993, Nelson finally settled his tab.
Wesley Snipes’ relationship with the IRS has been a tumultuous one. The saga began in 2006 when the actor was initially accused of tax fraud. Two years later, a federal judge sentenced him to three years in prison for willfully failing to file his tax returns. Snipes began his sentence in 2010 and was released in 2013. He soon dove back into his acting career with a role in 2014’s The Expendables 3 and, now, with a rumored role in another Blade film.
Fun fact: film legend Sophia Loren served 17 days in prison in 1982 over a dispute with the Italian authorities over her 1974 tax return. Here’s what happened: she declared less income that year because her compensation for the film Il viaggio was deferred, thus moving her into a lower tax bracket. Officials, however, maintained that she should have paid a higher rate. She appealed the ruling but still ended up being forced to serve 17 days (of a 30-day sentence). But in 2013 — nearly 40 decades after the dispute began — Italy’s Supreme Court finally cleared her of the tax evasion charges. So yes, she paid the right amount after all.
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