Hollywood stars who took on the tax man and won

When the tax man comes calling, avoiding jail time – and the headlines that come with it – is surely top priority for most stars. Unfortunately, Nicolas Cage had to sacrifice his Las Vegas residence when his house was foreclosed on by a bank in January 2010 after the IRS hit him with a massive tax lien.

The star owed $6.2 million in back taxes but avoided bankruptcy with a series of on demand action movies with the National Treasure star at their centre. An escape from debt worthy of its own film perhaps?

Lorraine Kelly is one of the luckiest on our list, escaping a £1.2 million tax tribunal case against HMRC in 2019.

HMRC argued the presenter was an ITV employee but ultimately the scales fell in Lorraine’s favour as the judge ruled she was a self-employed freelancer. He concluded her work on-screen involved performing a persona rather than being herself.

Brother to Alec, William and Daniel, Stephen Baldwin avoided paying the price of alleged state income tax evasion in prison time. 

The actor filed for bankruptcy in 2009 and in 2012 was arrested for alleged tax evasion. However, he’s still free to enjoy plenty of Baldwin family dinners, admitting he failed to file taxes for three years and agreeing to correct the debt.

Cast your mind back to 1990, when country singer Willie Nelson was billed $16.7 million in tax. Fortunately for Willie, his lawyer argued the sum down to $6 million once his assets had been seized. 

To clear up the remaining, much smaller, sum Willie released The IRS Tapes: Who’ll Buy My Memories in 1992 and cleared the debt by 1993.

Beloved pundit Gary Lineker won a 2023 appeal against HMRC when he was billed £4.9 million in tax, from both the BBC and BT Sport for 2013-2014 and 2017-2018.

HMRC argued Gary was an employee of both broadcasters but the judge ruled he was actually a freelancer and held contracts across both BT Sport and BBC.

In 1989, comedian Ken Dodd made headlines when he was charged with tax evasion at Liverpool Crown Court prompting a trial lasting three weeks. In the end, Dodd was acquitted of fraud but did pay the taxes due.

Years later, just days before the comedian died, he tied the knot with his partner and avoided an estimated bill of around £2 million as, generally, assets can be transferred to a surviving spouse or civil partner without tax.