Cashed Out

Having grown up in the spotlight and never learning how to be a responsible adult, Michael Jackson makes terrible financial decisions that jeopardize his career and wreak havoc on his personal life.

As a revolutionary singer, songwriter and record producer, Prince’s flamboyant life off stage proved to be just as covert and mysterious as his unresolved death in 2016. After his death, and leaving no will behind, Prince’s $200 million estate came be under attack. A vault in his Paisley Park home would be found to contain over $100 million worth of unreleased music, lyrics and rights that the estate and potential successors were ready to cash in. With 45 individuals coming forward claiming to be a wife, child, sibling or other relative, exhaustive legal battles would ensue trying to prove who the rightful heirs to the music icon's estate would be. Without a will, Prince’s legacy would be left in the hands of the court’s rulings, allowing the final chosen successors to exploit his brand, his record label and music library, however they deem fit.

Amy Winehouse was making an attempt to recover from heroin and alcohol addiction, but it is believed she was pushed to perform despite her mental, physical and emotional decline.

Johnny Carson, host of "The Tonight Show Starring Johnny Carson" for 30 years, had a reputation as a devious philanderer.

Robin Williams' life took on another downward spiral when he was diagnosed with Parkinson's disease after years of quietly suffering through severe depression and a deep-rooted drug and alcohol addiction.

Entering the studio system at 16, Debbie Reynolds becomes one of Hollywood's biggest stars; Reynolds, 84, passes away one day after the tragic death of her daughter, Carrie Fisher, prompting news outlets to report that she died of a broken heart.

Actor Paul Newman dedicated his time to changing the world, but on his quest to help those in need, he made a huge mistake when he let an outsider determine the fate of his family's legacy.

Muhammad Ali was an Olympic gold medalist, a prize fighter and heavyweight champion who is widely regarded as one of the most significant and celebrated sports figures of the 20th century. From the moment Ali lined his pockets with some money, people began to take advantage of him. From boxing promoters to religious leaders, everyone wanted a piece of “The Champ” – and they got it. Right before his death in 2016, Muhammad Ali painstakingly worked to create a plan that would guarantee his beneficiaries financial freedom. He never would have imagined that his last brawl would be between him and his family over his final wishes.

For over half a century, Riley B. King – better known as B.B. King – defined the blues for the world. But while he was a music pioneer and visionary, he was a novice at handling his money. Without much business sense, King struggled to collect royalties from his recordings during his lifetime, relying heavily on earning his wealth paycheck by paycheck, gig by gig. Even worse, he would waste his money on a severe gambling addiction that landed him in the hands of the IRS. By the end of his life. B.B. King had earned more than $100 million, but by the time he died in 2015, his net worth had dwindled to a relatively meagre $10 million. Following his death, a vicious war broke out between his 15 kids, their 15 different mothers(!), and his long-time manager LaVerne Toney, who was accused of poisoning and killing the him.