Famous musicians who are capable of producing hits and also filling stadiums all around the world seem to have quite the envious existences. They travel to what are deemed to be the nicest cities on the planet, they are beloved by millions of adoring fans, and they live in mansions that are, for the rest of us, unattainable homes. Musicians who make it to the top of their industries for any amount of time are worldwide stars who are recognized just about anywhere they go, and thus they seem to have made it to the mountaintop as it pertains to their professional and business lives.
Just as is the case in any business endeavor, things can quickly go terribly wrong for musicians who are atop the charts. In some cases, a person who hit it big with one song never again finds that kind of success, and thus his money dwindles away and is never seen again. Some other individuals are unable to help themselves during spending sprees. Stories of famous musicians who have gone bankrupt have made for television documentaries that attract attention from viewers, if for no other reason than the public loves to see the downfalls of celebrities because we cannot help but stare at those figurative car wrecks.
15 Dee Snider
14 Lauryn Hill
The former member of group The Fugees was one of the hottest solo acts in all of music after her The Miseducation of Lauryn Hill catapulted her to stardom. She found herself reporting to prison in 2013, however, after she was ordered to serve three months behind bars due to a failure to follow proper tax returns. U.S. Magistrate Judge Madeline Cox Arleo scolded Hill during the sentencing process, saying the following to Hill: “This is not someone who stands before the court penniless. This is a criminal matter. Actions speak louder than words, and there has been no effort here to pay these taxes.”
13 Dionne Warwick
One would have thought that Dionne Warwick would have been just fine in 2013. Her 50-year career had been filled with hits and also five Grammy Award victories, and Warwick also had a history of being involved with several charitable organizations. Warwick had fallen on hard times by the spring of 2013, however, so much so that she was “down to $1,000 in cash” when she filed for bankruptcy. That news followed what was reported to be decades of money mismanagement and possibly even denial of her actual financial realities.
12 Toni Braxton
11 Wayne Newton
Perhaps you think of Las Vegas or the phrase “Danke Schoen” when you hear or read of the name Wayne Newton. Newton also has quite the reputation for being unable to take proper care of his finances. The Vegas entertainer filed for bankruptcy in 1992, but it was believed that Newton was financially secure by the end of the decade. Security only lasts so long, however, as the IRS was looking to claim almost $2 million from Newton in 2005. Things got so bad by the end of 2012 that the Casa de Shenandoah that had served as Newton's massive estate was put up for sale.
10 Marvin Gaye
Tragedy seemed to follow Marvin Gaye regardless of the successes that he would come upon during his career. The man responsible for some of the most beautiful and even bone-chilling music of his time was forced to file for bankruptcy after he was left hurting from a divorce settlement. Gaye fell into depression and addiction later on in his life, and he was shot to death inside of his parents' home by his father. Haunted by personal demons despite all of the fame and money that he had made during his career, Gaye was thrust into peace in one of the saddest ways imaginable.
9 Cyndi Lauper
8 Tionne Watkins
Tionne Watkins is more known by those in the public as T-Boz. She was chosen to feature for the TLC trio that became one of the most successful women's music groups in history. All of that success was well into the past by 2011. Watkins quietly filed for Chapter 13 in February of that year, and she did so again later that year when she was unable to continue payment on mortgages. What was the third bankruptcy case of her life was later thrown out by a judge, offering another reminder that the mighty can crash and crash hard.
7 Jerry Lee Lewis
Anybody who has been performing for seven decades as has Jerry Lee Lewis is going to have some stumbles and even falls. The rock music icon who will be remembered for such hits as “Whole Lotta Shakin' Goin On” and “Great Balls of Fire” fell and in a big way back in 1988 when he was forced to file for bankruptcy. Lewis listed over $3 million in debts at that time. Nothing, not even bankruptcy, has yet been able to completely slow Lewis down as of the posting of this piece. He is still performing in the summer of 2015 at the age of 79 years old.
6 Willie Nelson
5 MC Hammer
4 Leonard Cohen
3 Courtney Love
The wife of deceased grunge rock royalty Kurt Cobain has been the subject of abuse for over two decades. Everything from drug use that she has publicly spoken about to her relationship with Cobain to the legacy of the rocker has landed Love negative headlines over the years. Courtney Love has insisted that she has gotten things together despite the fact that she allegedly squandered around $27 million of what was referred to as “Nirvana Money.” One reason to have doubts about Love's claim is that a psychiatrist accused the musician of owing him over $48,000 as recently as May 2015.
2 George Clinton
The music legend who is credited for being the mastermind behind Parliament and Funkadelic was not the most savvy of businessmen during the best days of his music career. George Clinton signed the rights for his music way during the 1980s, and he filed for bankruptcy in 1984. Perhaps the biggest blow to his personal finances came in January 2001 when a judge ruled that Clinton was not allowed to keep the rights to certain music that he wrote in the 1970s and 1980s. It was said at the time that the catalog of songs was worth over $100 million. Ouch.
1 Vanilla Ice
You have likely by now heard and read of the story of Vanilla Ice, one that is filled with a plethora of twists and turns that would make for an fascinating movie let alone a short piece of a list. He was responsible for the “Ice Ice Baby” song that was the only massive hit of his rap career, he fell on hard times in the 1990s, and he then turned his life around and even got involved in some television work. Robert Van Winkle again found himself in legal problems in February 2015 when he was accused of burglarizing an abandoned home. He accepted a plea deal in that case.