Top 10 Musicians Who Went Broke

In the mid-to-late 2000s it was impossible to turn on a radio and not hear the unmistakable sound of T-Pain’s auto-tuned voice. The Florida native was one of the hottest names in hip-hop at the time, and even picked up a couple of Grammys at the height of his fame. Despite his success, T-Pain was not immune to making poor financial decisions, many of which cost him dearly. In a 2019 radio interview, the rapper quipped that he “went from having $40 million in the bank to having to borrow money to get his kids Burger King.” T-Pain has since rebounded financially and claims that going from “mega-rich” to “super broke”, has taught him the true value of money.

David Crosby is as synonymous with rock n roll as the Fender Stratocaster. He broke through as a member of The Byrds in the 1960s, before becoming a full-fledged superstar as a member of Crosby, Stills & Nash. However, like many of his contemporaries, Crosby was an avid drug user. In the ‘80s he would enter into a downward spiral that included arrests for drug and weapons possession, driving under the influence and hit-and-run. By the mid ‘80s he was addicted to alcohol, cocaine and heroin (he later claimed to have spent millions on his drug habits), all of which contributed to a decline in record sales. Crosby eventually filed for bankruptcy and would struggle financially for many, many years.

This iconic ‘90s girl group landed atop the Billboard charts four times between 1994 and 1999. Songs like “Creep” and “Waterfalls” made them household names and brought them untold amounts of fame, success, and wealth. Unfortunately, that last one didn’t last very long. From the outside TLC was on top of the world, but upon further inspection it was revealed that costly medical bills, insurance payments, and bad business deals with their manager and record label had left them completely broke. The group filed for bankruptcy in 1995, with their debts clocking in at around $3.5 million. Sadly, this story does not have a happy ending, as founding member Lisa "Left Eye" Lopes died in a car accident in 2002 at the age of 30.

One of the most successful R&B singers of all time, Toni Braxton never met an award she didn’t win. The Maryland native took home her first Grammy in 1994 and her last in 2015, a testament to her resilience as an artist. Despite her continued success, Braxton has experienced her fair share of financial troubles. Like many of the artists on this list, Braxton’s recording contract favored the record studio, and she wasn’t making enough off of royalties to sustain her lavish lifestyle. She filed for bankruptcy in 1998 but bounced back in 2000 thanks to the success of her third studio album, “The Heat”. However, Braxton filed for bankruptcy a second time in 2010, after health concerns forced her to cancel her Las Vegas residency.

Since being discovered by the late rap legend The Notorious B.I.G. in the mid-’90s, Lil’ Kim has sold more than 15 million albums and is widely regarded as one of the most influential and important female rappers in history. Don’t worry, there’s a “but” coming. Buuuuuut she was also extremely frivolous with her money, purchasing any number of extravagant items that she simply could not afford. In 2018 Lil’ Kim filed for bankruptcy and it was revealed that she owed the government close to two million in back taxes and faced debts of up to $4 million. Who knew that the royalties from songs like "It's All About the Benjamins" wouldn’t be enough to pay the bills?

With a whopping ten top 10 singles to her name, including "TiK ToK", which was at one time the best-selling digital single ever, Kesha knows a thing or two about success. However, her much publicized lawsuit against her former producer, Dr. Luke, decimated her bank account. Legal fees don’t come cheap, and at one-point Kesha reportedly had to accept $250,000 from Taylor Swift in order to cover her legal expenses. But Kesha didn’t lose her magic touch when it comes to topping the charts. Her self-funded third album, “Rainbow” peaked at number one on the Billboard 200 chart and was certified Gold by the Recording Industry Association of America just four months after its release.

We don’t even know where to start when it comes to this rapper's financial troubles. 50 Cent, who never failed to produce stacks of cash for his music videos, filed for bankruptcy in 2015, with his debt listed at over $30 million. 50’s financial woes can be attributed to a number of factors. For starters, he was reportedly spending over $100,000 a month on lifestyle expenses. Second, he had recently been ordered to pay Lastonia Leviston $5 million for illegally releasing a sex tape of her online. Third, he screwed over his ex-business partner, causing a federal judge to order him to pay $17 million to him. And you know it’s bad when you file a lawsuit against your own lawyers for millions!

If this entry proves anything, it’s that you can be the most effortlessly cool and talented soul singer on the planet and still wind up behind the 8-ball. Marvin Gaye’s financial woes can be attributed to marital problems. The Rock and Roll Hall of Famer went through a famously troubled divorce from his first wife, Anna Gordy, in 1975, and quickly fell behind on his alimony payments – filing for bankruptcy in 1976. With no money to speak of, a judge ordered Gaye to pay his ex-wife with royalties from his next album. The album, entitled “Here, My Dear” did little to help his situation, and Gaye was faced with the possibility that he would be sent to prison for big back taxes he owed the government.

The peak of Lauryn Hill’s fame came in 1998. That was the year she released her seminal debut solo album “The Miseducation of Lauryn Hill”. The record was a massive critical and commercial success, garnering Hill five Grammys, including Album of the Year. However, a group of musicians called New Ark sued Hill on the grounds claiming that she “used their songs and production skills but failed to properly credit them for the work". It would take years for the lawsuit to be settled, and in the end Hill was forced to pay New Ark around $5 million. Ouch. Years later, Hill would famously serve three months in prison for failing to pay her outstanding tax bills.


Before we unveil our number one pick, here are some honorable, or dishonorable, mentions:

Harry Nilsson

Mick Fleetwood

Jerry Lee Lewis

Kelis

The rise and fall of MC Hammer is a cautionary tale many entertainers would be wise to remember. Hammer started in the ‘80s but truly burst onto the scene in the early ‘90s thanks to his album “Please Hammer Don't Hurt 'Em”, which included the mega hit “U Can't Touch This". Suddenly Hammer was loaded, and . . . he quickly went to work blowing his $33 million net worth on lavish items. He purchased a mansion and filled it with extravagant items and amenities, kept a staff of 200 people on his payroll (mostly friends, family and community members which to be fair, is a nice impulse), and found himself on the receiving end of multiple lawsuits. When he finally filed for bankruptcy in 1996 he was at least $10 million in debt. Moral of the story: don’t treat your bank account like a bottomless pit of cash.