Paul Newman is one of the most recognizable faces in the world – from his classic Hollywood films to the salad dressing aisle of the grocery store, his name famous blue eyes are inescapable. While most celebrities would be content with merely fame and fortune, Paul saw the lifestyle as a trap and dedicated his time to changing the world. But on the star’s quest to help those in need, he made a huge mistake when he let an outsider determine the fate of his family’s legacy. After Newman’s death, the man who he trusted to run his companies and take care of his daughters began to cut them out one by one, leaving a $600 million-dollar empire on the brink of collapse. Read less

Debbie Reynolds was one of the biggest stars of the final years of Hollywood’s golden age, entering into the old-school studio system at the age of 16. Yet after five decades gracing movie screens across the world, she passes away at 84, seemingly from heartbreak. News outlets reported that the famed actress couldn’t handle the sudden loss of her daughter, Carrie Fisher, whose death occurred just a day before. Amid all the success, both mother and daughter were intertwined in a world that Carrie once referred to as “Hollywood inbreeding”. Filled with some of early Hollywood’s biggest celebrity scandals and financial disasters, Debbie and Carrie would enter separate roller-coaster rides of tragedy and triumph. By the end of their lives, the motherdaughter duo would jointly be worth over $100 million. Yet while their family quietly mourned the loss of two generations, Disney would be searching for a way to bring the Star Wars princess back from the dead. Read less

Robin Williams was a legendary comedian, actor and entertainer who won over legions of fans by bringing some of Hollywood’s most beloved movie characters to life. However, the one person who he failed to make happy was himself. After years quietly suffering through severe depression and a deep-rooted drug and alcohol addiction, Williams’s life took on another downward spiral after he was diagnosed with Parkinson’s Disease. In the final months before his death, the star would become besieged by paranoia and began outlining a meticulous will and trust to leave behind for his family. Yet his death would be followed by a bitter eight-month feud between his true heirs and his third wife, who looked for a loophole to steal a piece his children’s rightful inheritance. Read less

Having grown up in the spotlight, and never learning how to be a responsible adult, Michael Jackson made terrible financial decisions that jeopardized his iconic career and wreaked havoc on his personal life. Shrouded in controversy, his death in 2009 may have been at the hands of a doctor administering lethal doses of anesthesia. However, what is even less transparent is how his entire estate ended up lining the pockets of two men who the Jackson siblings say Michael could not stand – industry veterans John Branca and John McLain. Read less

George Michael was an English pop music phenomenon and sex symbol who rose to fame as a member of the music duo Wham! However, staying at the top wasn’t easy. George Michael’s private life was revealed to the world when he was arrested for engaging in a lewd sexual act with a male police officer in Beverly Hills in 1998. The man that women around the world lusted after would eventually be forced out of the closet, and what followed was a public career and personal life filled with turbulence. Drug dependency, depression, paralysing grief, legal battles with his record company and even a brush with death would ultimately set the star far back from the spotlight. In 2016, Michael’s life would ultimately come to an end when his lover Fadi Fawaz discovered the singer dead in their UK manor from sudden heart failure. Over his 40-year career, George Michael had amassed a fortune in excess of $128 million dollars. Yet without a will in place, the controversies of the late celebrity wouldn’t end with his death. While he had been quietly donating millions to charity throughout his life, Michael’s estate and fortune would be left in question, as his relatives speculated whether or not his death was due to foul play. Read less

At 27, Amy Winehouse was on a collision course with death. While she was making an attempt to recover from heroin and alcohol addiction, Amy’s fate was accelerated by the people banking off of her earning power – especially her father. Pushing her to perform when she felt too weak, Mitch, along with Amy’s managers ignored the obvious mental, physical, and emotional decline of the vibrant soul singer. On Saturday, July 23rd, 2011, the star was discovered unconscious and without a pulse in her Camden Square house. Despite the British tabloids later reporting that Amy was worth anywhere from $15 to 20 million, the truth would soon be revealed that because of her hefty daily drug expenses, the value of her estate had dropped to a mere $4.6 million. What followed was a string of online scams and celebrity death pools all profiting off of her death. Meanwhile, Winehouse’s estate would turn into a source of contention as her remaining fortune would return to her parents, the very people who, perhaps inadvertently, pushed her closer to death. Read less

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. Read less

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. Read less

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. The circumstances surrounding his fatal overdose at 57 from the powerful opioid painkiller Fentanyl, remains largely unexplained, and who provided the star with drugs has never been determined. However, tracing back through his legendary career exposes a secret, ongoing drug addiction stemming from his relentless desire for perfection and power in the music industry. 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. Read less