It’s hard to feel bad for mega-rich celebrities trying to make a quick buck by cheating the government out of taxes. Unfortunately, sometimes it’s an honest mistake — especially when you’re dealing with millions coming from different businesses. While some celebs like R. Kelly blatantly abuse the system, some are too whacked out on drugs to even know what’s happening.
These celebrities all tried to evade their taxes and got caught — but one ended up serving time for tax evasion she didn’t commit.
Charlie Sheen Tried To Help Get Lindsay Lohan Out Of Tax Debt, But Failed
Lindsay Lohan had some difficult times in her life. With drug addiction, erratic behavior and problems finding work, the star found herself in some legal trouble with the IRS in 2012. Charlie Sheen attempted to dig his friend out of tax debt by paying her $100,000 – but it only covered what she owed for 2009. She still owed taxes for 2010 and 2011. Lohan’s tax problems were so severe that the IRS literally seized all of her bank accounts. Lohan owed a total of $233,904 after Charlie Sheen’s donation, but that’s nothing compared to some of her tax-evading celebrity peers.
Martha Stewart’s Legal Problems Inspired A Character On Orange Is The New Black
Long before lifestyle guru Martha Stewart ever served a jail sentence for insider trading at the cushy prison that inspired Orange Is The New Black, the media mogul failed to pay taxes on her East Hampton mansion. Stewart attributed her IRS woes to an honest mistake – she barely spent time at the residence. Imagine having so many homes that you literally forget one exists?
Stewart didn’t gain much sympathy from the IRS (they’re a fairly unsympathetic bunch). She was forced to pay $220,000 in pack taxes plus penalties to the State of New York.
Al Capone’s Tax Evasion Brought Down A Mob Empire
Al Capone was a powerful mobster — so powerful Scarface was literally written about him. Capone controlled a number of speakeasies and casinos in Chicago during the prohibition era. This wasn’t what did him in – it was actually some white collar crimes. Yes, even one of the most powerful, feared mobsters in the world isn’t a match for the IRS. In 1931, after spending a year in prison for weapons charges, the mobster was indicted for tax evasion. He pleaded guilty and was given an 11-year sentence. At the time of his sentencing, Capone owed $215,000 in back taxes plus a $50,000 fine.
Lauren Hill May Still Owe The IRS Money For Evading Taxes For Three Years
Lauryn Hill is a legendary hip-hop artist who has amassed eight Grammys in her decades-spanning career. Unfortunately, she failed to file her taxes between the years of 2005 and 2007, where she made an estimated $1.5 million. According to a Tumblr post written by the aging rap star, she was just doing what was necessary to protect her family from “hostility, false entitlement, manipulation, racial prejudice, sexism and ageism.” Hill pleaded guilty to tax evasion in 2012 and served a three-month prison sentence in 2013.
In 2016, news swirled that the singer, who took a break from the game at the height of her popularity in 2000, had IRS woes yet again. These reports were false, but for really tragic reasons. The financially struggling star was still working to pay off taxes from her original issues. It’s still nowhere near what Nicolas Cage owed.
Nicolas Cage Owed A Whopping $6 Million To The IRS
In 2012, action hero Nicolas Cage probably could have used some of the riches he found in National Treasure. The star was massively behind on his taxes and blamed his business manager for what he called “financial ruin.” Cage owed $13 million for taxes in 2002, 2003, 2004 and 2007. In 2012, he finally paid off over $6 million after selling a number of his assets, including his properties in California, Las Vegas and New Orleans, a couple yachts and a 67-million-year-old dinosaur skull that was worth $276,000. Cage later sued his business manager for the mess up.
Wesley Snipes Cheated The Government Out Of $7 Million
For some reason, Wesley Snipes believed he didn’t have to pay taxes because of an obscure section of the tax code that said foreign income wasn’t taxable for U.S. citizens. This was obviously misread by his accountant and Snipes was left with a massive unpaid tax bill. He failed to file taxes from 1999 to 2001, where he would have owed the government a whopping $7 million. In 2008, he was convicted of three misdemeanor counts for failing to file. He lost an appeal in 2010 and was sentenced to three years in prison.
Pete Rose’s Gambling Addiction Had Him In Hot Water
Ex-baseball Hall of Famer Pete Rose is a known gambling addict. After retiring from the field, Rose became a team manager and was met with much controversy after it was found that he gambled on baseball. Many argued his bets affected the way he managed his team. Is it really possible to rig a game of skill?
Though Rose struggled with the disease for years with his addiction, the IRS had little leniency when he failed to report gambling wins and income from selling autographs and memorabilia. Rose spent five months in prison after pleading guilty to federal tax evasion in 1990. Apparently, he didn’t learn his lesson and in 2004, he was hit with a nearly $1 million lien for unpaid back taxes.
Willie Nelson Let His Tax Bill Sit Until It Was $32 Million
Willie Nelson, the famed folk singer, ran into trouble with the IRS when he failed to pay a $16 million tax bill he was served in 1984. The IRS found that a number of his exemptions didn’t qualify, and the singer blamed the accounting firm who handled the paperwork. Though the IRS simply gave him a bill, the singer didn’t have $16 million in cash. He let the bill sit for six entire years, where it grew to $32 million after penalties and interest. The IRS was pretty lenient on Nelson, and allowed him to pay just $15 million.
R. Kelly Spent Most Of The ’00s Dodging Taxes
When he’s not busy urinating on underage girls or holding women hostage in his mansion, R. Kelly is evading taxes. The “Trapped In the Closet” singer has more than a few tax woes. In 2012, Kelly had nearly $5 million in IRS debt from 2005. In 2008, the singer paid $2.6 million in back taxes and another $1 million in 2011, but it wasn’t enough to cover his debt.
R. Kelly was hit with another tax lien for $200,000 after failing to pay income taxes in 2012 and one for 3.2 million after failing to pay in 2013 and 2014. According to documents, Kelly owed $146,532.96 from 2009, 2011 and 2012 alone. At a certain point, wouldn’t you get a new accountant?
Judy Garland Lost Her Home And Was Forced To Live In A Motel
Judy Garland was just 16 years old when she rose to fame starring in The Wizard of Oz — and she lived a life plagued with drugs, drinking and suicide attempts. To make matters even worse, the starlet ran into trouble with the IRS when she failed to pay taxes in 1951 and 1952. By the time her series The Judy Garland Show was canceled in 1964, the actress was $4 million in debt to the IRS, and they repossessed her home. Garland was forced to live in and out of hotels, and five years later she died of an unintentional overdose.
Pamela Anderson Was Hit With Two Separate Tax Bill
Pamela Anderson’s busty looks couldn’t get her out of trouble with the IRS when she evaded taxes in 2010 and 2012. Eventually, they’ll catch on and in 2010, she was hit with a massive tax bill for $1.7 million. The second time, it wasn’t just federal taxes the 50-year-old actress owed. She neglected to pay the state of California over $100,000 and the federal government over $250,000. Anderson may have played a lifeguard on TV, but there’s no doubt that she couldn’t save her finances. Hopefully, by 2017, she’s found a decent accountant and paid all of her dues.
Vanessa Williams Owed The IRS $300,000
Vanessa Williams’ career as the first black Miss America has been tarnished with scandal since she posed nude in Penthouse. She was able to catapult the controversy into a massive career in music, scoring Grammy, Emmy and Tony nominations for her work in TV and on Broadway. If only Williams could use her trouble with the law for even more success. If she could, she might have been able to pay her $369,249 tax bill. The IRS filed a tax lien against Williams for the aforementioned amount for failing to pay all of her taxes in 2011.
Marc Anthony Wasn’t Prosecuted – But Boy, Did He Owe
Jennifer Lopez seems like the type of in-charge woman that wouldn’t let her finances get out of control. Her ex-husband Marc Anthony apparently doesn’t take the same lead. The singer was unknowingly evading taxes from 2000 to 2004. Anthony raked in $15.5 million in those four years and was ordered to pay $2.5 million in back taxes. He was in supremely hot water for this error, and the threat of major jail time loomed over his head (hey, it happened to Wesley Snipes). Fortunately, the IRS didn’t think Anthony intentionally tried to cheat his taxes. He claimed his accountant must have filed the wrong forms. Anthony paid in full, and the charges were forgotten.
Sinbad Owed So Much That He Filed For Bankruptcy Again
As a comedian, Sinbad is hilarious, but his financial problems are nothing of the sort. The comedian rose to fame in the ’90s and quickly fell out of favor by the early 2000. This put a financial strain on the actor, who was faced with financial ruin after tax evasion finally caught up with him. In 2013, Sinbad was nearly $11 million in debt to the IRS and the state of California. He owed them $8 million and $2.33 million respectively for failing to pay taxes on income earned between 1998 and 2006. Unfortunately, Sinbad today makes nowhere near what he made in 1998 (though as of 2013, he still pulled in roughly $16,000 month which is no small chunk of change). He was forced to file for bankruptcy a second time.
Annie Leibovitz Managed To Pay Her Tax Debt With A Loan
Famed photographer Annie Leibovitz is credited with some of the most groundbreaking photoshoots of all time – from the Beatles to Angelina Jolie. Her body of work is astounding and so is the amount she owed the IRS and the State of New York. In 2009, it came to light that the photographer failed to pay taxes in 2004, 2006 and 2007. She owed the IRS $2.1 million and the state of New York $247,980. Leibovitz got a loan to pay off her debt, but in exchange, she had to put copyrights for every photo she’s ever taken and her four homes up for collateral.
Sophia Loren Spent Time In Italian Prison For Tax Evasion — But She Was Innocent
Sophia Loren is undeniably glamorous, and she probably looked great wearing orange. In 1982, the actress and singer was sentenced to 18 months in an Italian prison for evading her taxes. The sad part of Loren’s story is that unlike R. Kelly, who undeniably evaded taxes for the better part of a decade, Loren was innocent. In 2013, the Italian courts finally ruled that she was improperly prosecuted and jailed. Loren had always maintained her innocence through the decades, long after her sentence.
Mike “The Situation” Sorrentino May Be GTL-ing In Jail
Mike Sorrentino is better known by his nickname The Situation. From 2009 to 2012, the reality star was pretty busy tanning, hitting the gym and doing his laundry on MTV’s The Jersey Shore. The show that made him rich also sparked a few tax problems and he was charged with tax evasion and structuring (purposely making deposits of just less than $10,000 to fly under the IRS’ radar). Because of his charges, the entire cast of Jersey Shore was audited, but only Sorrentino was accused of skipping out on paying $8.9 million in taxes. To make matters worse, the indictment alleged that Sorrentino falsified business records to make it look like he owed less. That’s not just tax evasion, that’s tax fraud. Sorrentino’s case is ongoing, but he faces up to 11 years in jail and $600,000 in fines.
This “Survivor” Had To Survive A Prison Sentence For Tax Evasion
If you’ve survived in the wilderness, jail should be easy right? At least that’s what Richard Hatch hoped when the reality show contestant failed to pay taxes on his $1 million. To be totally honest, it’s kind of a bonehead move to publicly win a ton of money on one of the most popular TV shows on the planet and think no one would notice that you didn’t pay taxes on your winnings. Hatch was convicted in 2006 and sentenced to 51 months in prison. He was released in 2011 and later returned to jail very briefly for additional tax return charges.
Stephen Baldwin Actually Got A Pretty Lucky Break
Stephen Baldwin was arrested in 2012 for failing to file income taxes in 2008, 2009 and 2010. The actor owed a whopping $400,000 in back taxes but ended up getting a lucky deal. The court waived the added $50,000 in interest and penalties as well as reduced the total amount owed by another $50,000. Baldwin had to pay just $300,000. As long as he paid back the money within a year, he wouldn’t face any permanent damage to his record. If he didn’t he’d face five years of probation and get another five years to pay the money.
Darryl Strawberry was one of the most renowned players in Major League Baseball. He was also a violent husband, a drug abuser and a convicted felon. In December of 1994, Strawberry was indicted on three counts of tax evasion and conspiracy. By February 1995, he pleaded guilty to a single count of tax evasion after entering a plea bargain.
When Strawberry signed a contract extension with the Mets worth an estimated $7 million, it was to be paid out over 30 years after his career ended. Unfortunately, Strawberry had ongoing tax problems and faced debt from income earned in 1989, 1990, 2003 and 2004. The IRS ended up auctioning off this annuity. In 2014, the IRS set the minimum bid for the right to receive the remaining payments totaling $1.28 million at $550,000.