Five Famous Artists Who Went From Riches to Rags

The allure of wealth and celebrity is undeniable. We’ve all dreamed of being on the silver screen, or on stage in front of thousands of screaming fans, and of having access to the sort of incredible wealth that comes with being a globally recognized artist. Everyone loves to imagine themselves as the star of a rags to riches story at one time or another, but very rarely do we consider the difficulties of maintaining that lifestyle, or the consequences of poor wealth management. Whether through poor choices, bad advice, or just plain awful luck, the following five famous artists found themselves going from riches to rags, and in desperate need of financial help.

Willie Nelson

The famous country star infamously found himself in a pickle with the IRS in the early 1990s, due to some dubious tax strategies in the ‘70s and ‘80s. Facing a potential $16 million tax bill, Willie’s attorney was able to argue the titanic sum down to “just” $6 million. Unable to produce even that much, the country crooner soon found himself without home or hearth when the government seized his property in order to settle his debt. The ever optimistic performer was unbothered, and declared that he’d “be fine, as long as I got my guitar”.

Willie’s story, while fraught, ends on a happy note: adoring fans purchased his Texas home at auction, and it was returned to him in 1991.

Wesley Snipes

Known for heart-pumping action thrillers like Passenger 57 and Blade, in 2006 Wesley Snipes was confronted by a foe that not even the most hardened action star could hope to defeat: the Internal Revenue Service.

The ill-advised action star narrowly dodged two felony tax fraud convictions but caught three misdemeanor “failing to file” charges, spending the better part of three years in a minimum security federal prison.

Unfortunately, Wesley’s saga continues: in November of 2018, the US Tax Court ruled that Snipes was still $23.5 million in arrears, and rejected both his claim that he was unable to pay, and his offer to settle for the proportionally microscopic sum of $842,061.

Mark Twain

Not even legendary authors are immune to financial woes. Samuel Clemens, better known as Mark Twain, found himself declaring bankruptcy in 1895 following a series of disastrous investments.

By the time of his bankruptcy, the “Huck Finn” writer was the modern equivalent of $2.3 million in debt, a figure that he would quickly pay back with the proceeds from an enormously successful speaking tour.

While having narrowly dodged the poor house, Twain would never see the end of financial difficulties. He would bounce from poor investment to poor investment, and testifying in court just three years before his death would lament that he had been “swindled out of more money than there was on the planet.”

50 Cent

At the height of his fame, rapper Curtis “50 Cent” Jackson was worth a mind-boggling $155 million. Leveraging his image as an aggressive, devil-may-care street tough, 50 rose to be one of the best selling rap artists of all time, selling close to 30 million albums worldwide.

That same aggressive, performative excess would be his undoing when, in 2015, he found himself filing for Chapter 11 bankruptcy.

50 Cent’s financial woes stemmed primarily from an opulent lifestyle that saw him shelling out nearly $200,000 a month in living expenses, and a series of court decisions that saw him over $32.5 million in debt, which calls for some serious help from credit repair services.

Michael Jackson

The troubled Prince of Pop found himself millions of dollars in debt, following a number of highly publicized trials and an increasingly bizarre series of eccentric and lavish purchases.

Though Jackson had a steady and substantial stream of income from royalties and other investments, it wasn’t enough to keep up with his opulent, storybook lifestyle, and he began to borrow heavily from close friends in order to avoid the spectacle and indignity of bankruptcy proceedings.

While the exact figure is unknown, some estimates put Michael Jackson’s debts as high as half a billion dollars at the time of his death.