Celebrities That were Imprisoned for Tax Evasion

The recent changes to the US tax code has dominated the news, and not without reason. Those changes will likely make life every difficult for a significant number of people. But it’s clearly a touchy subject and not one I want to dip my toes into, especially not as a Brit who is witnessing it from the outside and won’t be affected by it (although we have our own controversies to deal with right now).

Instead, I thought I would be a good time to switch the focus to people in those high tax brackets that didn’t have it quite so easy.

Chuck Berry

The rock and roll legend was no stranger to prison. In the 1960s he spent time behind bars for transporting a minor across state lines and in the following decade he was sentenced to four months for tax evasion. Throughout this successful music career he had seemingly insisted that he be paid in cash, which means there was no paper trail, no taxes and no money for the government. They didn’t take too kindly to that.

Darryl Strawberry

The Major League Baseball star was sentenced for tax evasion in 1995 after failing to pay $100,000 in taxes and failing to report more than 3 times that amount in income. The income came from autograph signing events and promotional appearances as opposed to his wages, but at this time he was earning a salary of nearly $2 million and in the early 1990s this reached over $4 million, which makes those undeclared earnings a costly and somewhat stupid oversight on his part.

Ja Rule

Ja Rule decided to go all out and simply not file his tax returns for two years, resulting in massive unpaid taxes and an eventual prison sentence of over 4 years, which ran concurrent with a charge for gun and drug possession. It wasn’t the first time he had been in trouble with the law (he had previously been arrested for assault, drug possession and driving with a suspended license) and a few years after his release the legal challenges continued.

In the summer of 2017 he launched the Fyre Festival, which was an unmitigated disaster and resulted in dozens of lawsuits and an indictment for fraud.

Richard Pryor

The legendary comedian had many issues throughout his life, including drug and health problems. But the burden of unpaid taxes and legal threats hovered over him as well. In the 1970s he was sentenced to 10 days behind bars when he “forgot” to pay his taxes, responding to those charges with the coolness and humor that personified this comedian.

Lauren Hill

Arguably the most famous of all celebrity tax controversies, the former Fugees singer ended up with a 3 month prison sentence for failing to pay more than $1.5 million in taxes. Those taxes were owed on her earnings from 2005 to 2007, a good decade after the breakthrough hit Killing me Softly. By the time 2005 rolled around, Hill had dipped in and out of the limelight and was making a living with sporadic touring, often showing up late for concerts and not exactly winning praise from critics or fans.

A $1.5 million tax bill means she was still earning a sizable income during this time, but she claimed to have lived “very modestly” in spite of this. How you can live modestly with a few million in the bank I’m not sure, but after spending time in prison and then under house arrest, and after paying back all of those back taxes, she is no doubt living much more modestly these days.