Music Stars Who Died Penniless

We all have a certain image that pops into our heads when we hear the phrase "rock star," one with many components: throngs of fans with devil horns or lighters in the air, tour buses full of groupies, copious amounts of drugs and alcohol, and material excesses that would make a rich CEO blush. Lavish wealth has always been part of the rock and roll lifestyle, and this is true even for those who project a public image of gritty, working-class realism. For example, take New Jersey boy and blue-collar hero Jon Bon Jovi, who got rich enough singing about poor, struggling Johnny who scrapes by working on the docks, to buy an arena football team. 

This is not to say, however, that those who are fortunate enough to stack a ton of chips in the music business are always wise enough to manage those chips prudently. A shocking number of very famous, very accomplished musicians have gone from rags to riches right back to rags again, and while some have managed to claw their way back to the top, others were not so lucky, taking to their graves little more than the lint in their pockets.

In the annals of popular culture, perhaps no one has become a more unlikely superstar than Sammy Davis Jr. He was a diminutive Black man, missing his left eye due to a car accident, who sashayed his way into the hearts of audiences of all colors at the height of the Jim Crow era; a member of the Rat Pack, the coolest of the cool kids, who palled around with Frank Sinatra and Dean Martin; a star of the silver screen; and a recording artist with multiple top 20 hits. He was also a rare famous, Black convert to Judaism, and was married to a Swedish model at a time when interracial relationships weren't exactly the status quo — a man who, in short, marched to the beat of his own drum, and did it with style.

Upon Davis' death from cancer in 1990, it came to light that he had been not just broke, but massively in debt to the IRS to the tune of over $5 million. In a strange turn of events, a Hollywood man whose driver's license had recently gone missing discovered that it had apparently been used to rent a storage locker in his name — and in that locker, authorities found a treasure trove of valuable items that had belonged to Davis, including vintage instruments, a jukebox, and an old record player. The IRS promptly seized the locker's contents, though police said they didn't expect any arrests to follow. 

Not many session musicians find themselves showered with riches and notoriety, but if ever one should have been, it's guitarist David Williams. He had been in the business since he was a teenager, strumming for the likes of the Dells and the Temptations, and his career really took off once he came to the attention of producer Quincy Jones, whom you may have heard of. Jones put Williams to work in the studio for a pair of records which you also may have heard of — "Off the Wall" by Michael Jackson, and its follow-up, "Thriller," which of course went on to sell approximately six ker-billion copies. That's Williams playing that ultra-funky, galloping riff in the middle of "Billie Jean," and aside from the King of Pop, he worked with a murderer's row of iconic artists such as Stevie Nicks, Paul McCartney, Herbie Hancock,  Madonna, Mariah Carey, and Whitney Houston, to name a few.

After experiencing a medical issue in March 2009, Williams was taken to a hospital in Hampton, Virginia — where his family says he received insufficient treatment due to a lack of insurance and resources. "David, who supported [pop stars] onstage all those years, [had] nothing," a family friend told Page Six. "[His family] just wanted him to have some integrity, and instead the hospital was despicable at best over his lack of insurance." Williams passed away in the hospital at 58 — a fate ill-suited to a music legend.

Billie Holiday was simply one of the greatest vocalists there has ever been, and her story — as documented in her autobiography "Lady Sings the Blues" — is the stuff of legend. From one-time prostitute to singer in Count Basie's orchestra to solo sensation, all within the space of a dozen years in the 1930s and '40s, Holiday became a formidable presence on the national music scene not just in spite of the racial prejudice that was running rampant in the industry and the country at that time, but while actively confronting it. Her 1939 recording "Strange Fruit," a haunting indictment of racism, became her signature tune — but it was that racism which, unfortunately, contributed to her premature death.

Holiday was the target of a years-long campaign of harassment by the FBI, which was at the time heavily focusing on users of street drugs, with a predominant bias toward those of color. Holiday struggled mightily with a heroin habit that drained her finances and did damage to her career, even serving a brief prison sentence in the late '40s. According to the book "Chasing the Scream: The First and Last Days of the War on Drugs," the Bureau — led by the notoriously racist Harry Anslinger — continued to hassle Holiday even as she lay dying in the hospital, and she passed away with only $750 in cash, which was reportedly strapped to her leg, and which she had intended to offer the nurses who had cared for her. She was only 44 years old.

If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

The younger brother of Robin, Maurice, and Barry Gibb (also known as the Bee Gees), Andy Gibb became a superstar in his own right during the disco era of the late '70s. Thanks in part to the crack songwriting talents of Barry, Gibb became the first male solo artist to have his first three singles shoot to No. 1 on the pop chart, and he also carved out an enviable career as a TV personality and appeared in a Broadway production of "Joseph and the Amazing Technicolor Dreamcoat." By the '80s, though, his professional fortunes had begun to seriously wane — and this, combined with an out-of-control cocaine habit, combined to leave him in dire financial straits. In 1987, he filed for bankruptcy, and his finances never recovered.

Having conquered his addiction after a stint in the famed Betty Ford Center, Gibb was preparing to launch a comeback in 1988 — but that was not to be. Years of cocaine abuse had taken its toll on his heart, and in March of that year, he was admitted to the hospital after falling ill. Just days later, he was dead of a heart inflammation brought on by a virus at only 30 years old.

If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

In the 1940s, big bands ruled the popular music landscape, and Woody Herman was a bandleader extraordinaire. A clarinetist, Herman was the leader of the First Herd; a rollicking outfit, the Herd contributed such standards as "Northwest Passage" and "Caldonia" to the American songbook. Herman's success continued into the decades beyond, with new iterations of his band (dubbed the Second Herd, the Third Herd, and finally the Big New Herd, of course) dabbling in new styles of music, up to and including rock. Herman was a three-time Grammy winner, and a consummate professional; in 1976, he marked his 40th anniversary as a bandleader with a bash at Carnegie Hall. By the next decade, though, his fortunes had completely reversed, thanks to irresponsible management.

In the late '70s, Herman popped up on the radar of the IRS due to the fact that, during the previous decade, his manager had failed to pay taxes on the salaries paid to Herman's band. As a result, Herman was forced to continue touring and performing well past the age when most folks would have been enjoying their retirement, just to satisfy his debts. Even as his health began to fail in the mid-'80s, he remained onstage, though he eventually delegated bandleader duties to his trusted sideman, Frank Tiberi; in 1987, after more than five decades of entertaining crowds around the nation, Herman passed away from emphysema and pneumonia at the age of 74.

It may seem inconceivable that one of the most successful recording artists of all time would be deeply in debt at the time of his death — but then, Michael Jackson was almost as famous for his jaw-dropping spending habits as he was for his music (and his legal troubles). He of the expansive Neverland Ranch, pet chimpanzee, and hyperbaric oxygen chamber also did not exactly see his demise coming; Jackson was only 50 when he died in 2009, and was in the midst of preparing for an epic comeback tour which might have helped to right the financial ship. An insomniac, Jackson was being "treated" by notorious doctor Conrad Murray, who would eventually be convicted of involuntary manslaughter for providing Jackson with the drugs that killed him — a lethal mixture of sedatives and the powerful anaesthetic propofol.

During a 2013 wrongful death trial brought against promoter AEG Live by Jackson's family, forensic accountant William Ackerman testified that Jackson's spending had gotten him into an absolute ocean of debt, according to the Los Angeles Times. The King of Pop was, he testified, spending $30 million per year on debt payments alone. During the last eight years of Jackson's life, his debt had ballooned by $170 million, and his total liability when he died was in the neighborhood of a half billion dollars. He further testified that Jackson's 1990s tours either broke even or lost money, while his spending continued at a steady pace. Jackson was "tapped out," Ackerman said — and it took three full years after his death for his estate to satisfy his financial obligations.