Most people imagine their lives would be better with endless wealth. After all, how amazing would it be to have all of your basic needs met, and then plenty of spare change left over for the shiniest cars, first-class vacations, a designer wardrobe and enough cash to buy your way into any event, party, restaurant or exclusive location in the world?
While it’s nice to have enough money to cover everyday life expenses, it seems that excess wealth can’t – and doesn’t - always buy people out of all of their problems. If anything, money can complicate lives beyond a point that most human beings, wealthy or not, know how to deal with.
Sadly, money also cannot buy a cure for everything. Many wealthy people have battled with depression, anxiety, substance abuse, or have suffered from poor relationships (or lack of any real relationships) in their lives. As a result, even those who are filthy rich have problems just like anyone else. Here are some people, from celebrities to business tycoons, to royalty and wealthy heirs and heiresses, who discovered the hard way that fortune and success doesn’t always lead to happiness.
12 Howard Hughes, tycoon, aviator, filmmaker and philanthropist
11 Casey Johnson, Johnson & Johnson Heiress
Casey Johnson, the great-great granddaughter of the co-founder of the multinational pharmaceutical company Johnson & Johnson, spent a lot of her life in the pages of tabloids and society gossip columns and struggled with a myriad of problems during her relatively short life. Johnson was famous for partying with Paris Hilton and was even engaged to reality star Tila Tequila. No wonder she was a mainstay in the press: she was the centerpiece of several controversial stories, from allegedly burglarizing a friend’s home, to having a public falling out with her aunt after she accused her aunt of stealing her boyfriend. Johnson also refused to seek treatment for drug abuse, and was cut off financially by her family. At the age of 30, Johnson died of diabetic ketoacidosis, which was a complication caused by untreated diabetes.
10 Marilyn Monroe, actress
Perhaps no one is a bigger Hollywood legend than Marilyn Monroe, one of the 20th century’s biggest sex symbols and one of the most iconic figures in American culture. However, by most accounts, the beautiful blonde had a sad, if not disturbing, private life. Many of her biographers have written that Monroe had psychological issues and found it difficult to cope with fame. In fact, her life was quite difficult from the onset: she didn’t have a father and had a mentally unstable mother, then she grew up in foster homes, and as a teenager was reportedly sexually assaulted. As an adult, she might have made it as one of Hollywood’s biggest stars and had an estimated net worth of $27 million, but continued to be sad despite her fortune: she was married three times, but all three marriages ended in divorce. She suffered from miscarriages. The final years of her life were filled with illness, personal problems, and an overall poor reputation. The circumstances of her death at age 36 are still contested and have been classified as a probable suicide.
9 Anthony Marshall, an heir to the Astor fortune
The Astor family was one of the wealthiest families in the United States in the 19th and 20th centuries. However, even wealth can’t guarantee the happiness of all members of one of America’s most distinguished families. As one of the family matriarchs, Brooke Astor, struggled with Alzheimer’s towards the end of her life, according to accounts in the press, her son Anthony did not provide for her. He allegedly allowed her to live in squalor while siphoning around her fortune. In 2009, he was convicted of this crime and sentenced to 1-3 years in prison. He reported to prison in 2013 at the age of 89, although he was later released for health reasons.
8 Frank Sinatra, singer
Although “old blue eyes” provided many people with a lot of happiness through his beautiful, soulful music, he was plagued with unhappiness throughout his life. His son, Frank Jr., has commented to the press that his father was withdrawn and often seemed sad, and his daughter, Tina, has written that she feels he could have benefited from anti-depression drugs. Sinatra is said to have suffered from depression and from mood swings throughout his life. The singer even attempted suicide twice in 1953, once after he had a fight with his second wife, Ava Gardener, and then again later that year.
7 Jesse Livermore – the “boy wonder” of Wall Street
Back in the early 20th century, Jesse Livermore was famous for making and losing several multi-million dollar fortunes. As a result of his work on Wall Street, Livermore was incredibly rich: he was worth $3 million and $100 million after the 1907 and 1929 market crashes, which, adjusted for inflation, would mean that he would have been worth billions of dollars today. However, he somehow managed to lose most of his trading capital (it was never disclosed how he managed to do so). By 1934, Livermore was bankrupt and suspended as a member of the Chicago Board of Trade. In the end, he committed suicide.
6 Diana, Princess of Wales
The woman whom the world watched get married to Prince Charles in a “fairy tale” wedding lived anything but a fantasy; she suffered many personal and private setbacks in the public eye during her marriage, divorce and at the end of her life. Diana, who once said that she wanted to be the queen of people’s hearts, experienced a tumultuous personal life in the public spotlight. Her struggles culminated with her marriage to Prince Charles crumbling in the 1990s and her death in 1997. Sadly, the end of her illustrious life ended up being far from a fairy tale, even though she had married into royalty and had given birth to the future King of England.
5 Cameron Douglas, actor
Cameron Douglas is the oldest son of actor Michael Douglas and grandson of legendary actor Kirk Douglas, and has played a few roles in films. Although he grew up with a life of privilege thanks to his famous Hollywood family, he has battled addiction for most of his life and has spent years in and out of prison. He was arrested for drug offences at least three times and is currently in prison, where he is serving a sentence for drug possession.
4 Cory Monteith, actor and singer
On stage and on television, Cory Monteith seemed to have everything: a starring role on the successful television show “Glee,” a great singing voice, acting talent and a relationship with co-star Lea Michele. Although he was worth at least $2 million at the time of his death (and would have been worth several million more in a few years as a result of his "Glee" success), money, love and support couldn’t help him succeed in his personal struggles. Monteith had been struggling with substance abuse since he was a teen. Before he passed away of an overdose in July 2013 in Vancouver, he had again been seeking treatment for addiction, but had clearly lost the battle.
3 Andre Agassi, tennis player
On the court, tennis legend Andre Agassi seemed to be unbeatable during his heyday in the 1990s and early 2000s. The superstar was very successful and earned tons of money (he's currently worth $175 million), and was even ranked World No. 1. But in his 2009 book, Agassi revealed that his life as a tennis superstar was one that he hated. He says that despite his wealth and success, playing the game interfered with his personal relationships and he felt disconnected with his life. He then became very involved in philanthropy and was especially interested in education. He opened the Andre Agassi College Prep Academy in 2001 and has said that he finds that work far more fulfilling than he did during his days as a tennis star.
2 Michael Jackson, singer
The legendary singer and performer has been said to have battled various demons throughout his life that no degree of fortune (he was worth $600 million in 2013) and fame could rid him of. Before Jackson's death in 2009, he supposedly had financial difficulties and was clashing with the promoters of a series of concerts, "This is It," that he was preparing to put on. His two bodyguards also wrote a book following his death that painted a picture of him as a sad, lonely superstar who had desired a more normal life.
1 Charles M. Schwab, chairman of Bethlehem Steel
Schwab’s name is familiar to us even today: back in his day in the early 20th century, he was a steel magnate. He began his career as an engineer in Andrew Carnegie’s steelworks and later ran Bethlehem Shipbuilding and Steel Company. The company became the largest independent steel producer in the world under his leadership. A controversial risk taker, Schwab’s risks paid off and he was awarded medals and entered halls of fame for his lifelong work in the steel industry. He also became staggeringly wealthy, moving to New York City and rewarding himself with a mansion that was worth $7 million at the time. He also owned estates and traveled in an expensive private rail car. However, money doesn’t always guarantee long-term happiness. Over several years, he spent most of his fortune, which was estimated between $25-$40 million at the time (or up to $800 million when adjusted for inflation today). What money he hadn’t squandered by 1929 he lost in the stock market crash. His home was seized and at the time of his death he was in debt and his holdings were worthless, prompting him to borrow money to make ends meet.