These days there are infinite ways to become rich and famous. The spawn of reality television in the ’90s created a new breed of celebrity unique to this generation. From media moguls famous for a home movie to YouTube superstars to former MTV VJs, stardom is a destination with more accessible roads than ever. Of course, most upper echelon celebs took the traditional route to stardom. Being awesomely talented, otherworldly beautiful, born into perfect circumstance, or all of the above, will lead to fame in any generation.
No matter how one achieves his/her fortune, one thing is certain: being insanely rich is one of the best deals going. Love, passion, and inner peace are great, but I’d definitely achieve nirvana the first time more than one comma appeared on my bank statement. Wealth brings freedom, and freedom breeds creativity. A flush bank account also leads to tons of free time and a lot of confidence in how to use it. When you’ve mastered one field, why not try your hand at another, right?
Diversification is important for any portfolio, but it also increases risk. Someone might be the greatest musician or the best Instagram twerker ever, but that’s no guarantee for success in the hotel business. In this list, you’ll find celebrities of all types – athletes, models, actors, reality stars – who bit off more than they could chew and paid a handsome, embarrassing price.
Here are 10 Celebrities Who Made Idiotic Investments.
10. Bono – Lost $140 M With PalmPilots
As the frontman for Irish rock band U2, Bono is one of the most famous people on Earth. U2 has sold over 170 million albums, won more Grammy Awards (22) than any artist in history, and was a first ballot Rock & Roll Hall of Fame inductee. The music-hating outcasts among us might know Bono as the 2005 TIME Person of the Year, a generous philanthropist, or successful venture capitalist. No? Well, he was also immortalized as a character on both The Simpsons and South Park. Bono is a big deal.
But fame and fortune can’t always shield celebs from bad business decisions. In 2004, Bono bought a large stake in Elevation Partners, a private equity firm heavily invested in Palm, Inc. Bono controlled a 30% stake in Palm, the company that introduced suburban mothers everywhere to PalmPilots – digital, handheld “assistants” that, in hindsight, were about as functional as carrying around a physical calendar. Bono was sitting pretty with Palm stock worth roughly $325 million, but the company botched the launch of its first smartphone. The iPhone became a thing, and Palm stock dropped from $18 to $5.70 a share. After the dust settled, the Joshua Tree singer had lost $140 million.
9. Jay Z – J Hotel
Similar to Bono, it doesn’t get bigger than Shawn Carter aka Jay Z. Jay is one of the greatest rappers ever while also having sold over 100 million album copies worldwide. In fact, only two artists in the genre have outsold him: Eminem and Kanye West.
Besides his personal music endeavors, Jay Z is a proven businessman and entrepreneur. He founded Roc Nation and Roc Nation Sports, entertainment and sports management companies, respectively. He’s also a certified sports agent, a club owner, and successful clothing line founder. Oh, and he’s married to Beyonce. And they have an exceptionally named daughter – Blue Ivy. Suffice it to say, Jay Z’s got it made in the shade.
Jay Z did, however, have one brutal investment fail. Back in 2007, Carter launched an effort to break into the luxury hotel business. “J Hotels” purchased property in New York City’s Chelsea neighborhood with plans to build a 150,000 square-foot hotel. Construction stopped when the 2008 recession hit, the company defaulted on a $52 million loan and was disbanded in court. Jay Z bounced back, but this was an embarrassing endeavor for a rapper who was still trying to establish himself as a respected New York City businessman.
8. Kim Basinger – Lost $19M Buying A Town
Most people’s dreams of wealth entail cars, yachts, mansions, and beautiful partners with whom to indulge in the fun. Some folks might envision an island in the Caribbean or even swan-diving into a pile of gold coins a la Scrooge McDuck. But have you ever thought about owning your own town? Is that even legal?
In short, yes. Actress Kim Basinger purchased the town of Braselton, Georgia for $20 million in 1988. Basinger became a household name in the ’80s as a model and then starred in films like L.A. Confidential, Batman, Never Say Never Again, and The Natural. After accumulating more money than she knew what to do with, Basinger purchased most of the land in Braselton (1,691 acres) with the goal of turning the town into a tourist attraction, including movie studios and a film festival. The bold plan didn’t last long, crumbling as quickly as it came to fruition. In 1993, Basinger sold the town for $1 million for a total loss of $19 million.
In unrelated news, Basinger was later robbed of more millions by ponzie scheme crook Bernie Madoff. Her bank account took another hit, but Kim managed to bounce back, continuing a respectable on-screen career with roles in countless films and even an appearance in Playboy.
7. Torii Hunter – Failed Floating Furniture Company
Stop me if you’ve heard this one before. Young athlete becomes a prep All-American in baseball, basketball, football, and track. He chooses to pursue baseball, blossoming into one of the most exciting players in the game, a perennial All-Star and Gold Glove award winner. Rather than invest in some lame conservative growth fund, the All-Star decides to swing for the fences and invest in inflatable furniture rafts.
Yep, you read that correctly. Torii Hunter didn’t lose as much money as most of the stars on this list, but his investment choice is definitely the most comical. At least, Kim Basinger wanted her own town. Torii just wanted to comfortably ride down a lazy river.
Hopefully losing $70,000 on a failed floating furniture company led the future Hall of Famer to hire an investment manager.
6. Wesley Snipes – Lawsuits For Quick Cash
Wesley Snipes has been one of the most recognizable actors in Hollywood for nearly three decades. Snipes broke into television in the late ’80s and achieved stardom with 1990s films like Major League, New Jack City, and White Men Can’t Jump. Snipes’ career peaked in 1998 when he starred in Blade, the cult-classic vampire action thriller that grossed $150 million worldwide and birthed the Blade trilogy.
The 2000s, however, were not so kind to Wesley. There was no one embarrassing investment in particular, but he went down as dark a hole as any star on this list. In 2005, Snipes filed a lawsuit against the producers and director of Blade for cutting his screen time in the third installment. This lawsuit, along with a 2005 effort to fight television personality Joe Rogan, led to much speculation on Snipes’ financial health.
In 2006, the hammer dropped. Snipes was charged by the federal government for conspiracy to commit fraud and tax evasion. He avoided felony charges but was still sentenced to three years in prison for failure to file tax returns, serving his time from 2010-2013. Since his release, Snipes has starred in Expendables 3 and Chi-Raq while countersuing the IRS to avoid paying $18 million in back-taxes.
5. Nadya “Octomom” Suleman – Questionable Pregnancy And Adult Films
What happens when a single mother of six chooses to get pregnant again via In Vitro Fertilization and ends up with another eight babies? Here in America, she gets famous, of course. And then she goes broke. And then she does adult films.
We were first introduced to Nadya Suleman in 2008 when she was dubbed “Octomom,” the miraculous woman carrying eight healthy miracle babies. Octomom became a sensation and, like most celebrities, was quickly overexposed. It was soon discovered that Suleman already had six young children, was unemployed, living on government assistance, and became pregnant with the octuplets courtesy of very questionable medical ethics. The healthy children were a miracle; the mother, not so much.
After numerous failed reality television stunts, welfare fraud charges, and filing for bankruptcy, Octomom decided to make an extreme investment in herself. Suleman starred in the Wicked Pictures’ adult film Octomom Home Alone in 2012. Exact figures on the investment pay-off are unavailable, but the film did earn four AVN award nominations.
4. Curt Schilling – Green Monster Games Mess
Curt Schilling was one of the most accomplished pitchers in modern baseball history. A 6-time All-Star, 3-time World Series champion, and one-time World Series MVP, Schilling etched himself forever in baseball lore when he led the Boston Red Sox to a championship in 2004 while pitching on an injured ankle. His performance that year is so famous that the “bloody sock” from his injured leg sold for $92,163 at auction.
Schilling was a certified bad-ass on the baseball diamond. When it comes to business ventures, a bad-ass Mr. Schilling is not. Curt made over $100 million during his 19-year MLB career. In 2006, he used $50 million to found Green Monster Games, a video game company that went belly up in 2012 when Schilling defaulted on a $75 million loan from the state of Rhode Island. Schilling was forced to sell off most of his possessions and now works as a baseball analyst at ESPN, where he is currently serving an indefinite suspension for a general display of ignorance and intolerance on social media.
3. Chamillionaire – Houston Home Turned Worthless
Chamillionaire made a name for himself as an underground rapper in Houston before taking the national hip-hop scene by storm with his hit single “Ridin'” in 2005. “Ridin'” reached #1 on the Billboard 100 and won Best Rap Video at the 2006 MTV Video Music Awards. He hasn’t been able to achieve any comparable mainstream success since, but Chamillionaire did invest in a string of successful auto dealerships and start his own record label – Chamillitary Entertainment.
In 2010, however, Chamillionaire was forced to default on his 7,500 square foot Houston mansion. The rapper says that the $2 million home became worthless, and he had to eat the loss. Unlike other stars on this list, it might be wise to trust Chamillionaire’s judgement. This year, he was named “Entrepreneur-in-Residence” at Los Angeles-based venture capital firm Upfront Ventures. Only time will tell if a Chabillionaire name change is in order.
2. Mike Tyson – Extreme Lifestyle
Mike Tyson earned a ridiculous $400 million over his 20-year boxing career. So, how much is left? According to the esteemed staff here at TheRichest, Iron Mike’s net worth is only $1 million. One million bones is nothing to scoff at, but for a man who used to make $30 million per fight, it’s basically nothing.
In his prime, Tyson was the most electric heavyweight to ever step in a ring. In terms of pure entertainment and raw punching power, his only rival was Muhammad Ali. Due to drug addiction and legal trouble, Tyson fell off hard in the 1990s. Recently, though, he has appeared in numerous movies, written a best-selling memoir, and starred in an acclaimed one-man Broadway show. So, where’s the dinero? Sadly, Tyson blew countless sums on his young, unsustainable, foolish lifestyle. Tyson filed for bankruptcy in 2003, and is still recovering from $23 million in debt that includes back taxes and divorce settlements.
1. Nicolas Cage – Castles, Snakes, And Shrunken Heads
The most entertaining way to make horrible investments is by simply spending all your money on crazy stuff. That’s exactly what Hollywood’s worst best actor – or best worst actor? – Nicolas Cage has done. As a member of cinema’s first family, Nick Cage (originally Nicolas Coppola) has been engulfed in a celebrity lifestyle since birth. If your uncle created The Godfather, you might act like a made man, too.
Cage has appeared in over 81 films, produced 12, and earned over $150 million during his career. Yet, he only has a net worth of $18 million. An insane spending habit and aversion to government collections agencies are to blame for Cage’s embarrassing loss of worth. Cage owes about $6.5 million in back taxes and has spent over $100 million on lavish purchases, such as: an $8 million castle in England, two albino king cobras, nine Rolls Royces, 30 motorcycles, a $17.5-million mansion in Bel Air, decorative shrunken heads, and numerous private jets.
Hey, Nick Cage’s money is Nick Cage’s money. With performances like Gone In Sixty Seconds, National Treasure, Wicker Man, and Ghost Rider, Cage has earned the right to spend his money. But, that doesn’t make his spending habits any less embarrassing.