When musicians hit it big, they can become millionaires (or even billionaires) if they manage their money well. But having so much money can be difficult, and it’s easy to make major, expensive mistakes. Those poor decisions cost these musicians millions, and many lost their entire fortunes and even had to declare bankruptcy.
Pop superstar Billy Joel sued his former manager, Frank Weber, in 1989. Joel’s lawsuit sought $30 million in compensatory damages for money that Weber had allegedly stolen. The suit also sought $60 million in punitive damages. Details from the filing include allegations that Weber gave out $2.5 million in loans without Joel’s knowledge or approval, double-billed Joel for music videos, created phony financial statements that were given toJoel, and even mortgaged Joel’s copyrights for $15 million without disclosing that information on the financial statements.
Partridge Family star, David Cassidy, filed for bankruptcy in 2015. Cassidy, who sold more than 30 million records, reported that his debt totaled up to $10 million. His filing listed creditors including Wells Fargo Bank, American Express, and CitiBank. Cassidy battled substance abuse issues during his life and died in 2017.
Rapper MC Hammer, the superstar behind the famous “U Can’t Touch This” tune, was earning $30 million per year by 1991 and had an estimated $70 million. But Hammer went on a spending spree, buying 17 luxury cars, two helicopters, 21 race horses, and a private jet. He bought a Fremont, California property for $12 million, then spent $30 million on renovations. Hammer spent at a rapid pace and filed for bankruptcy in April of 1996, selling his home for $6.5 million and losing his cars, planes, and horses.
Country music legend Willie Nelson has recorded more than 60 studio albums and ten live albums during his career. But in 1984, the IRS started to examine Nelson’s tax returns. The IRS noted that Nelson was claiming significant tax shelter investments, which were eventually determined to be illegal. Nelson was assessed $6 million in taxes plus $10 million in interest and underpayment fees. Those fees and penalties had almost doubled by 1990, prompting the IRS to seize his property to put it up for auction. Nelson released a compilation album called The IRS Tapes: Who’ll Buy My Memories? Nelson shared revenue from the album with the IRS to pay off $3.6 million of his debt. He ultimately paid off the remaining balance with income from other projects.
Singer, songwriter, and pianist Jerry Lee Lewis became a rock ‘n roll icon with his singles “Great Balls of Fire” and “Whole Lotta Shakin’ Goin’ On,” making him multiple millions of dollars. But when Lewis married his 13-year-old cousin, his career took a major hit and his success waned. Lewis pivoted into country music with hits like “To Make Love Sweeter for You” and “Me and Bobby McGee.” Despite his newfound success, Lewis had trouble with the IRS. In the 1870s, the IRS seized property from Lewis, then charged him with an overdue tax bill for nearly $2 million in 1988. Lewis was forced to declare bankruptcy and died in October of 2022.
Mick Fleetwood, the drummer for Fleetwood Mac, should be a multi-millionaire. Fleetwood Mac’s five albums sold roughly 55 million copies. But Fleetwood lost millions of dollars to a drug habit and impulsively bought homes including a $400,000 Hawaii property and a $1.8 million farm in Australia. He admitted to spending $8 million on cocaine over the years, and ultimately had to file for bankruptcy in 1984.
Lead singer of the Isley Brothers, Ron Isley found himself in major financial trouble when he didn’t file his taxes for years. The Rock and Roll Hall of Famer owed $5 million in back taxes, prompting the IRS to seize his yacht and vehicles in 1997. Isley declared bankruptcy. In 2006, Isley was sentenced to prison for, once again, failing to file his tax returns.
Since making antisemetic remarks in 2022, rapper, songwriter, and fashion designer Kanye West has lost a massive amount of money. West professed on Instagram that he lost “2 billion dollars in one day.” In a single week, West lost partnerships with Adidas, The Gap, and Balenciaga. TJ Maxx pulled his products from the shelves, and Apple Music pulled his Essentials playlist. While the exact amount of money that West has lost is unknown, Billboard reports that West has likely fallen from billionaire to millionaire status.
Michael Jackson died in debt, despite his massive career success. The King of Pop’s career started at the age of six, but Jackson spent lavishly on zoo animals, art, travel, gifts, and more. He also made large charitable donations. Jackson was heavily in debt by the time of his death in 2009, and had been making $30 million annual payments on that debt.
Rapper 50 Cent enjoyed a massive career, thanks to hits like “Candy SHop” and “in da Club.” He built an investment portfolio and was estimated to be worth $155 million after tax at the peak of his career. He earned $100 million from his shares in Glaceau VitaminWater when it was purchased by Coca-cola, and he founded film production companies G-Unit Films and Cheeta Vision. While 50 Cent had found many ways to invest and build on his fortune, he declared bankruptcy in July of 2015, reporting a debt of $32.5 million. He lost millions in lawsuits, including a failed deal with Sleek Audio that cost him $17 million. In addition to making bad business deals, he renovated an 18-bedroom mansion in Connecticut and purchased several luxury cars, leading to the loss of most of his fortune.
