Mob boss Al Capone earned his nickname running a crime syndicate in Chicago during the Prohibition. Bribery, prostitution, smuggling, bootlegging liquor and gunning down rivals were just some of Capone’s many crimes. But Capone’s skill was not just in breaking the law, it was in covering his tracks. And it was tax evasion that finally got Capone locked up; in 1931 he was sentenced to 11 years in prison. He served most of his sentence at the infamous Alcatraz prison, and died shortly after his release.
Country singer Willie Nelson developed a reputation as a free thinker early in his career. In the 1970s he rebelled against the Nashville sound to become a pioneer of country outlaw. He’s been known for activism on issues including the environment, animal rights and legalizing marijuana. In 1990, Nelson ran into real trouble with the government: The IRS seized his assets and informed him that he owed $16 million in unpaid taxes. Nelson sued his accountants when he discovered he hadn’t paid his taxes in years. After releasing The IRS Tapes: Who’ll Buy My Memories to raise cash, Nelson paid off his debts to the IRS by 1993.
Actor Wesley Snipes became famous for action movies like Blade, Demolition Man, and the sports film White Men Can’t Jump. In October 2006, Wesley Snipes and two accountants were charged with tax evasion and conspiring to defraud the government. The IRS said that Snipes had even filed false tax returns in an attempt to get a larger refund. Snipes was acquitted on two felony counts, but he was found guilty on three misdemeanor counts of failing to file federal income tax returns. Snipes is currently serving out a three-year sentence at a medium-security federal prison in Pennsylvania.
At the height of her fame, actress Sophia Loren was considered one of the most beautiful women in the world. In 1962, she became the first person to win an Academy Award for Best Actress for a non-English speaking performance. Twenty years later, though, Loren made headlines for something very different. An Italian court found her guilty of failing to report 5 million lore on her income tax return for 1970. Loren and her husband, renowned producer Carlo Ponti, had been under investigation for tax violations for several years. Loren made an appeal to Italy’s president for a pardon, but failed to receive one. The actress eventually served 18 days in prison.
Businesswoman and real estate entrepreneur Leona Helmsley was nicknamed “the Queen of Mean,” a reputation she spent decades earning. Helmsley was notoriously cruel to the people around her, especially her many employees. She was investigated and convicted of federal tax evasion in 1989, and spent 19 months behind bars. When her former housekeeper testified against Helmsley, she was famously quoted as having said, “We don’t pay taxes. Only the little people pay taxes.” Helmsley died in 2007, and left $12 million to her dog, while cutting two of her grandchildren out of her will.