The entertainment business is one of the most lucrative in the world. But talent, even intelligence, does not necessarily translate to investment savvy, and frankly money management is not an easy skill to learn. And there are always a number of scams and con artists ready to separate the newly wealthy from their money. Here are eight celebrities who are much better at making money than at keeping it.
One of the most recognizable names in movies has the reputation for taking any and every role that comes along, no matter how ridiculous — which makes sense since he has spent money on everything from fancy planes to dinosaur fossils. He lost his shirt during the 2008 real estate collapse when he had to unload five houses (including one formerly owned by Dean Martin and an allegedly haunted house in New Orleans) and three genuine castles. It’s estimated he burned through $15 million dollars per year for a whole decade.
A musician with more money than fiscal acumen, U2’s frontman Bono has seen his fortune come and go like the tide. His investment company, Elevation, made some great earnings at first, but one of his early investments was in Palm — which created the handheld personal assistant tablet the Pilot. Palm Pilots were everywhere, even before Blackberry took the same route, but all that changed when the smartphone was built, combining a cell phone with a PDA. Bono lost almost $450 million on the investment. He’s done better since, investing in Facebook and Forbes.
This singer turned entrepreneur, also known as Beyonce’s husband, is one of the most powerful celebrities today. He is a music producer with a multi million-dollar fashion empire. But once he tried his hand at real estate, attempting to build a hotel in New York’s historic Chelsea district. Unfortunately he too was a victim of the 2008 real estate crash and he ended up losing the property in court to the bank along with an undisclosed amount of compensation. He’s definitely bounced back though… as long as he stays away from real estate. Although, looking at the other entries on this list, that’s probably good advice for just about everyone.
When this Oscar-winning actress decided to invest some money, she really went for it: in 1989, she bought Braselton, an entire town in Georgia. At that time, Georgia was an up-and-coming filming location, so she thought to revitalize the town with its own film festival and movie studios. It would have been nice if she’d pulled it off but five years later the project was dead and she sold the town at a massive loss. Unlike the others on this list, she didn’t bounce back after that; she followed this up with an even worse investment, courtesy of scam artist extraordinaire Bernie Madoff.
Once the biggest name in women’s figure skating, when this Olympic Gold Medalist turned pro she starred in the touring spectacle known as “Ice Capades.” When the organization fell on hard times due to low attendance and a changing attitude toward figure skating, Hamill decided to invest in the company and save it from bankruptcy, but it was too late and she ended up going bankrupt herself two years later. She’s still in the skating business though, only now she teaches kids at skating camp.
She’s made millions from her singing career, but she’s had to file bankruptcy twice after spending that money like water. The first time she was $5 million in debt, which she recovered after releasing a new album… but her second bankruptcy, covering bad spending habits and a worse habit of not paying taxes, was for $50 million. She got out of that one by downsizing from a mansion to an apartment and appearing in a short lived reality TV show to pay off the debt.
This member of Hollywood royalty was an avid collector of movie memorabilia. Wanting to share her collection with the world, she decided to open a museum. Unfortunately, the museum was in a Las Vegas casino, and even worse, the casino wasn’t even on the Strip. Despite performing live on her own stage, neither she nor the collection proved popular enough to make any money and the property was sold off in bankruptcy — to the World Wrestling Federation (now the WWE). She also sold off some major pieces of her collection, including the iconic subway dress Marilyn Monroe wore in the movie “The Seven Year Itch.” She recovered financially later on with a successful memoir, but she tragically died of a stroke one day after Carrie Fisher — her daughter by actor Eddie Fisher — passed away in 2016.
This guy wasn’t just a hip hop artist — in the 1990s he was a phenomenon. His hit single “U Can’t Touch This” made him his first $30 million, and from there it just kept getting better. A million dollar mansion, race horses, cars, planes, even helicopters — you name it, he bought it. And when the money ran dry, he had to file bankruptcy. He’s doing much better now that he’s learned a thing or two about business investing, especially in tech companies like Twitter and YouTube.