16. Harry Nilsson
> Died: 1994
> Circumstances at death: Net worth listed at -$1 million
The singer-songwriter, who was born with congenital heart problems, died of heart failure at 52 after filing for bankruptcy. Most of his fortune was swindled by his former manager, who was eventually imprisoned for stealing millions from multiple clients.
17. Billie Holiday
> Died: 1959
> Circumstances at death: $750 in her bank account
The jazz legend, who repeatedly lent money to her mother to open a restaurant, was also plagued by legal troubles — which led to her being banned from performing in any venues that sold alcohol. Targeted by the FBI for her heroin addiction, she died surrounded by police guards who were serving drug possession charges.
18. Andy Gibb
> Died: 1988
> Circumstances at death: Reportedly millions in debt
The youngest of the three Bee Gees, Andy Gibb had some success as a solo artist, but it was short-lived. His depression and drug addiction led to lost opportunities as his binges took precedence over his work. The young singer ended up bankrupt and died at 30 from myocarditis caused by years of cocaine abuse.
19. Charlie Parker
> Died: 1955
> Circumstances at death: Reportedly penniless
The pioneering jazz saxophonist and composer developed an opiate addiction after fracturing his spine in a car accident. He struggled with mental health issues and gained a reputation for being unreliable, ultimately sabotaging his career. Parker died at 34 of pneumonia and a bleeding ulcer. The doctor who performed an autopsy on him reportedly thought Parker was a man of 60 based on the condition of his body.
20. Dana Plato
> Died: 1999
> Circumstances at death: Net worth of $1,000
The “Diff’rent Strokes” actress, whose fortune was stolen by an accountant, struggled with drug and alcohol addiction for much of her career. After losing most of her money, she was arrested for robbing a video store. Plato died at 34 from a prescription drug overdose.