15 Musicians Who Went Broke

13. 50 Cent

50 Cent probably shouldn’t be “In Da Club” any time soon – bottle service isn’t cheap! The rapper filed for bankruptcy in 2015, claiming to owe nearly $30 million to various creditors, among them Lavinia Leviston, a Florida woman who sued Jackson for $5 million in damages for doctoring and circulating her sex tape.

If that weren’t classy enough, Jackson has continued to post photos on Instagram showing off his luxury cars and literal piles of cash. When asked by a judge why he would be showing off wealth despite having filed for bankruptcy, Jackson admitted that the bills were actually prop money and rides were rented. However, some still doubt that Jackson really is broke; fellow rapper Method Man, who knows a thing or two about owing money, dismisses Jackson’s supposed financial woes as a “tactic” in order to protect his fortune and avoid paying his debts.

Buckets of Love no big deal this short paper. Lol #EFFENVODKA #FRIGO #SMSAUDIO

A photo posted by 50 Cent (@50cent) on

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14. Billy Joel

Like many people, Billy Joel took on a second job when he ran into money troubles and, in his own words, became a “realtor to the stars.”

Joel owed the U.S. government a few million in back taxes but couldn’t pay his bill because “the money that [he] thought was there wasn’t there.” Joel’s fortune had suffered over the years due to unfair record deals, mismanagement by his former brother-in-law as well as a series of costly divorces. So, to make things right, Joel sold his swinging NYC pad to fellow rock star Sting, his Hamptons home to comedian Jerry Seinfeld, and his Martha’s Vineyard property to J. Crew CEO Mickey Drexler.

The “Piano Man” took over his own finances, toured extensively and was able to pay his bill and then some.

Anthony Correia / Shutterstock.com

Anthony Correia / Shutterstock.com

15. Cyndi Lauper

She told us all about how “Girls Just Want to Have Fun,” but before that, this girl just wanted to pay her electric bill. Cyndi Lauper made a name for herself in the ‘80s and was the first female artist to have four singles in the Top Five all from one album. Not long before that, though, the singer had filed for bankruptcy after her split from the band Blue Angel.

Lauper joined the rockabilly-style group as a songwriter and lead singer and was with them for four years without much success despite the band’s solid New York fan base. Their self-titled 1980 album was released by Polydor but wasn’t much of a seller, nor was their second album which led to the group’s dissolution. The band members were later sued by their manager for $80,000, which forced Lauper to file for bankruptcy and work jobs in retail and perform at a piano bar. Fortunately for Lauper, her real big break came in 1983 when she released her first solo album She’s So Unusual, and the rest is history.

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