Plenty of household names have had runs-in with the tax authorities – whether by unwittingly entering into dubious avoidance schemes, failing to settle a bill, or blatantly trying to avoid paying their fair share. Read on to uncover 32 of the most infamous cases.

In 1974, the late actor and stand-up comedian Richard Pryor spent 10 days in a Los Angeles county jail for non-payment of taxes. Pryor reportedly had no valid explanation for failing to pay and simply told the judge that he forgot to file his tax return.

In 1982, screen legend Sophia Loren was jailed for 30 days – of which she served 17 – by an Italian court for allegedly underpaying taxes on her income in 1974. Loren's legal team appealed and she was eventually pardoned by the Supreme Court of Italy in 2013.

The reality star had the State of California tax authorities on her back in 2010. KoKo was accused of owing $18,490 (£13.7k) in taxes from 2007, which she claimed was an oversight on the part of her accountant. She speedily paid up and hired a new accounting team.

In 2011, singer and reality TV star Kelly Osbourne was reportedly hit with a $30,000 (£22.2k) bill for back taxes owed to the State of California. The State claimed the taxes dated from 2009, the year Osbourne appeared on Dancing with the Stars. 

Martha Stewart received a five-month jail term in 2004 for insider trading, but in 2002 the lifestyle queen was forced to pay the State of New York $220,000 (£154k) plus fines to cover taxes she failed to pay for her home in the Hamptons.

Australian rapper Iggy Azalea hit the big time in 2014, scoring her first top 10 hit in the US. Unfortunately, she didn't pay her fair share of tax stateside and in 2016 the IRS issued Azalea with a $391,056 (£290k) lien. She was reportedly later issued with a second lien for $269,980 (£200k). But she hit back at critics, tweeting in 2019: "I have a green card and pay taxes."

The troubled actress has had several major run-ins with the taxman, getting in trouble with both the State of Californian Franchise Tax Board and the IRS. Highly-publicised incidents include Time magazine’s revelation that Lohan owed $233,000 (£173k) in back taxes, while in 2017 she was found to owe $100,000 (£74k) from missed payments throughout the 2010s.

Lohan hasn’t had to pay it all back herself though, as fellow hell-raiser Charlie Sheen gifted her $100,000 (£74k) in 2012 to help pay off the debt. Lohan’s mother Dina then went on to file for bankruptcy in 2018 after declaring she was also drowning in $1.5 million (£1.1m)-worth of debt. 

The first winner of US TV show Survivor, Richard Hatch was awarded a prize of $1 million (£741k) in 2005 but failed to pay any tax on his winnings. The IRS duly got involved and Hatch was found guilty of tax evasion and sentenced to six years in jail. A serial offender, he has since served two further jail terms for tax evasion.

In 2013, actor Stephen Baldwin was threatened with prison for not paying New York state taxes to the tune of $400,000 (£296k). He was given a year to pay up and managed to meet the deadline and avoid jail. After several smaller tax incidents in recent years, Baldwin has paid out a total of $429,186 (£318k) to clear his debts.

The model-turned-animal rights activist got in trouble with the IRS as well as the State of California tax authorities for failing to pay thousands of dollars in owed taxes, and had liens placed on her properties. Anderson avoided further penalties by agreeing to pay back the debts, which included $439,000 (£325k) in personal income tax, in instalments.

Former supermodel Christie Brinkley got into trouble with the IRS in 2011. The authorities issued her with a $531,000 (£393k) tax bill and put a lien on her $30 million (£22.2m) home in the Hamptons, New York. Brinkley put the non-payment down to an accounting error and promptly paid off her debt.

Unable to sell his New Mexico ranch, Val Kilmer experienced severe money issues in the noughties, and the IRS allegedly filed a $538,000 (£399k) lien against him in 2009. The following year the actor was issued with a $500,000 (£371k) bill for unpaid federal taxes and a $68,000 (£50.4k) lien from the State of California for unpaid taxes. The actor sold the claimed property the following year and was finally in a position to clear the debts.

Ozzy and Sharon Osbourne didn't waste any time paying off an outstanding tax bill of $1.7 million (£1.3m) back in 2011. The State of California placed a lien on their main property, forcing the couple to settle their debt or risk losing their $12 million (£9.4m) Los Angeles home. Sharon reportedly blamed financial advisers for the misstep and said she hoped the move didn’t reflect negatively on the Osbournes’ “moral character”.

Hip-hop artist Lauryn Hill has hit the headlines for her tax problems more than her music over the last decade. In 2012, Hill was charged with three counts of tax evasion and spent three months in jail for failing to pay $1.8 million (£1.3m).

In 2002, three-time Wimbledon champion Boris Becker was busted for claiming to be a resident of Monaco when he was in fact living in Munich, evading $1.95 million (£1.53m) in German taxes. The court gave him a two-year prison sentence suspended for three years and a €500,000 fine, the equivalent of $819,500 (£607k) today. It also made him pay all trial costs.

Becker was declared bankrupt in 2017. But in September 2020, he was charged with concealing assets including £1.2 million ($1.5m) in cash and an apartment in high-end Chelsea, London. He was eventually found guilty in April this year and sentenced to two-and-a-half years in prison. 

In the 80s and 90s Robert Downey Jr was in the throes of alcohol and drug addiction. But he also had an alleged $2 million (£1.5m) tax bill hanging over him. Luckily Downey freed himself of his addictions and was then able to tackle his debt.

The IRS came knocking on celebrity photographer Annie Leibovitz's door in 2009 to recoup unpaid taxes totalling $2.1 million (£1.6m). The same year she also found herself unable to pay back a $24 million (£17.8m) loan and was teetering on the edge of bankruptcy before the terms were renegotiated.

Already in jail for an attempted possession of a weapon charge, rapper Ja Rule was sentenced to an additional 28 months behind bars in 2011 and fined $1 million (£741k) for neglecting to file tax returns between 2004 and 2008. Fast-forward to 2019 and fellow rapper 50 Cent fuelled rumours that Rule owed the IRS $2 million (£1.5m) in back taxes, spanning 2005-2008 and 2016. Twitter users were then quick to highlight the irony of Rule promoting Value Tax, a tax preparation company he later took ownership of. 

Singer Marc Anthony has been in trouble with the tax authorities on more than one occasion. In 2007, he was issued with a demand for $2.5 million (£1.9m) in back taxes. Three years later, the State of New York ordered him to pay $1.8 million (£1.3m), which he settled in 2011.

The acclaimed film director behind Raging Bull, Taxi Driver and The Wolf of Wall Street hasn't had as much luck with the tax authorities. In 2002, unpaid taxes of up to $1.9 million (£1.4m) reared their ugly head, but he quickly paid them off. However, nearly 10 years later Scorsese was then hit with yet another tax bill in 2011, costing him $2.85 million (£2.1m).

The world-famous FC Barcelona soccer player was convicted of tax evasion in July 2016 and handed a 21-month prison sentence, as well as a €1.7 million ($2.1m/£1.5m) fine. Messi’s team used secret offshore bank accounts to hide payments for his image rights, cheating the Spanish taxman out of €4.1 million ($5m/£3.7m) from 2007 to 2009.

In 2017, the Spanish courts traded the prison sentence for a €252,000 fine ($307k/£228k) – the equivalent of €400 ($488/£461) for each day he would have spent in jail. But Messi wasn't the only one in trouble. His father also received a fine of €1.3 million ($1.6m/£1.2m), as well as a 15-month prison sentence for helping his son to avoid taxes. Messi’s father also avoided serving time behind bars as his sentence was swapped for a €180,000 ($220k/£163k) fine in 2017.

When the King of Pop died in 2009 his executors said his estate was worth a meagre $2,105 (£1.5k), arguing that his reputation had been left in tatters following child harassment allegations and other unflattering press coverage. However, the IRS came up with a different figure – an incredible $161 million (£113.7m).

Following a four-year legal dispute, the US Tax Court ruled that the correct figure for Michael Jackson’s posthumous fortune was $4.1 million (£2.9m) in 2009, which leaves the estate with unpaid taxes to settle. And even after he passed, Jackson's estate has been raking in millions. In fact, the Jackson estate has been the highest-earning celebrity estate each year since 2010, peaking in 2016 when it generated $825 million (£590m).

However, when he died it's estimated Jackson had debts of $500 million (£353m), which then passed onto the estate. Jackson left most of his estate to his mother Katherine and his three children, who have since paid off some of his debts.

In 1987, record-breaking British jockey Lester Piggott was locked up for three years for defrauding the taxman out of £3.25 million ($5m), the equivalent of £9.2 million ($12.4m) in today’s money. Piggott used several pseudonyms to channel his earnings into offshore bank accounts in the Cayman Islands, Switzerland, the Bahamas and Singapore. At the time, the resulting trial and prosecution was the biggest individual income tax-dodging case Britain had ever seen.

The American singer's messy divorce from husband Martin 'Kendu' Isaacs in 2018 revealed that she had built up a hefty $6.5 million (£4.8m) in back taxes between 2008 and 2016. The singer continued to flounder on the tax front, and in 2019 she was revealed to have stacked up another $1 million (£741m) in unpaid federal taxes in 2016 and 2017.

Portuguese football icon Cristiano Ronaldo got into a spot of bother with the Spanish tax authorities from his time playing for Real Madrid. By failing to declare earnings from advertising contracts at the time, Ronaldo avoided paying €5.7 million ($6.9m/£5.1m) in taxes. In 2019, the star was fined €18.8 million ($22.8m/£17m) by the Spanish authorities as part of a deal that meant the football star avoided a 23-month jail sentence.

Plagued by poor financial management, Nicolas Cage's accounting team neglected to pay $14 million (£10.4m) in back taxes during the 2000s. The IRS demanded the cash in 2009, and the actor reportedly only cleared the debt earlier this year. The actor does have a penchant for splashing out, and his big-ticket purchases include two European castles costing $10 million (£7.4m) and $2.3 million (£1.7m) respectively, and a $150,000 (£111k) Superman comic.

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Lil Wayne is clearly in need of a good accountant. The hip-hop artist was stung for back taxes of $1.1 million (£840k) in 2010, a further $7.7 million (£5.7m) in 2012, and the mother of all tax bills in 2014 when the IRS accused him of failing to pay an eye-watering $12 million (£8.8m). At a show in 2018, Lil Wayne told the crowd that he had to thank singer Jay-Z, who had allegedly helped him with his sticky tax situation. In 2019, he reportedly spent $14 million (£10.4m) settling his tax debts.

Cheating on his tax returns for years, the IRS finally caught up with actor Wesley Snipes in 2006, and he was charged with fraud. The case lasted two years, and in 2008 the Blade actor was sentenced to three years in prison for his crimes. Over the next decade Snipes had a series of tax run-ins, culminating in an unpaid bill of $23.5 million (£17.4m). Claiming he couldn’t afford the enormous sum, Snipes offered $842,000 (£624k) for the bill to be wiped which, unsurprisingly, was rejected by courts.

British singer-songwriter Gary Barlow (pictured) and his Take That bandmates Howard Donald and Mark Owen, along with their manager Jonathan Wild, hit the headlines in 2014 after it was discovered that their earnings were being channelled into a dubious music industry 'investment' scheme to avoid tax. As a result, Barlow and co were ordered to pay back more than £20 million ($27m) to the UK's tax authorities.

In 1990, country star Willie Nelson was hit with one of the largest individual federal tax bills of all time, a huge $32 million (£19m), the equivalent of $63.7 million (£47.2m) in today’s money, which his lawyer negotiated down to $6 million (£3.6m) after his assets had been seized. Unable to pay, Nelson released The I.R.S Tapes: Who'll Buy My Memories? album in 1992 to help settle the bill, which was cleared by 1993.

At the beginning of 2021, the estate of late pop legend Prince was found to owe $32.4 million (£24m) to the tax authorities, after its executors massively undervalued the star’s assets. The IRS believes that the singer was worth $163.2 million (£121m) when he died in 2016 – almost double the $82.3 million (£61m) originally calculated by trustees. Tax collectors have also added a $6.4 million (£4.7m) fine to the bill, which will be paid off by his six siblings, who are heirs to the musician’s fortune, because of the inaccuracy of the initial calculations.

The final years of the Wizard of Oz star’s life were scarred by money troubles. In 1964, the State of New York slapped Garland with a $4 million (£1.4m) bill – the equivalent of $33.6 million (£24.8m) in today’s money – for unpaid taxes dating from the 1950s. Garland couldn't pay, the authorities repossessed her home, and she ended up living in hotels until she died of tragic circumstances in 1969, aged just 47.

 

In June this year, former footballer Samuel Eto'o was hit with a 22-month suspended prison sentence after being found guilty of tax evasion. Between 2006 and 2009, Eto'o failed to pay the Spanish Public Treasury €3.9 million ($4m/£3.3m), a tax he should have paid on the income generated by the transfer of his image rights from Puma to Barcelona. He's reportedly repaid a portion of the sum and admitted he owes the money, but has claimed his former agent – who's also been handed a one-year suspended sentence and €905,155 ($948k/£777k) fine – was responsible for the tax evasion. 

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