Expensive vodka seems like a pretty sure bet, if you’re a celebrity trying to make a couple extra million. Maybe just stick with that next time.
Britney Spears Learned You Can’t Out Bubba the Gump
In 2002, she opened up Nyla, a Cajun-inspired restaurant in New York City. Within five months, she ducked out of the venture due to “management’s failure to keep her fully apprised,” as well as bad reviews and health-code violations.
Stan Lee Never Quite Figured Out Web Marketing
He started Stan Lee Media, an online production and marketing company, in 1998. Within two years, he’d file for bankruptcy and his business partner would run off to Brazil as he was being investigated for questionable company stock transactions.
If You’re Gonna Come for the Colonel, You Best Not Miss
Flava Flav opened a fast-food restaurant called Flav’s Fried Chicken in Iowa in 2011, but things went south almost immediately, and he and his partner launched dueling legal action against one another. When the dust settled, Flav was allowed to open two more locations in Las Vegas and Michigan, but both went under quickly as well.
Natalie Portman’s Vegan Shoes
She teamed up with shoe company Te Casan to launch a $275 vegan high heel, and the company folded less than a year later.
Jay Z Couldn’t Turn a Warehouse Into a High-End Hotel
In 2007, he bought a Manhattan warehouse that used to belong to a cable company with the intention of making the first of many J Hotels — boutique hotels for the bougie. Two years later, he and his partners defaulted on their $52 million loan, and spent the next few years battling each other in court.
Planet Hollywood, But Make It Fashion
Supermodels Christy Turlington, Claudia Schiffer, Elle Macpherson and Naomi Campbell collaborated on a high-end chain restaurant in places like Rockefeller Center and Piccadilly Circus. It was called Fashion Cafe, and featured some of the models’ most iconic outfits. They never managed to break even and the business crumbled.
Lenny Dykstra Hasn’t Even Begun to Hit Rock Bottom
His post-MLB career included failed ventures from car washes to a jet charter service for professional athletes. He was dogged by allegations of fraud and money laundering, and was eventually indicted by the feds. He then wrote a book about it — and was promptly sued for allegedly not paying for the book’s social media campaign.
Kanye’s First Fashion Line
Kanye came up with an idea for horrible clothes as far back as the early aughts, called Pastelle. He rapped about it in one of his songs, wore a branded varsity jacket to an award show in 2008, and then cancelled it just after pictures of his garbage clothes started circulating online.
Don Johnson Can’t Run (or Name) a Venture Capital Company
The Miami Vice star started a company called — tragically — Timber Doodle Glade Equity Venture LLC. He went into debt, owing thousands of dollars on groceries alone. A bank sued him, and he had to file for bankruptcy just to keep his house.
Debbie Reynolds’ Terrible, Horrible, No Good Very Bad Deal
The legendary actress and singer renovated an old Las Vegas joint and opened up the Debbie Reynolds Casino and Hotel. The casino part did as well as you’d expect in Vegas, but she was only making money off the hotel part, which at one point was losing as much as $450,000 a month.
Burt Reynolds Couldn’t Stop Buying Restaurants
He invested in a chain called PoFolks, which grew to over 100 locations at one point, but eventually crumbled and left him $20 million po-er. He tried his luck again with a chain called Daisy Diner, but that sucked another $10 million out of his pocket.
They Go Together Like Baseball, Rhode Island and Video Games
MLB great Curt Schilling and co. took out $75 million in loans for a Rhode Island-based video game company, 38 Studios. Schilling spent $50 million of his own money to produce one game called Kingdoms of Amalur, put the company in $150 million debt and forced taxpayers to cover the vast majority of that.
Mark Twain Invested in the A.I. of His Day
Twain made a small investment in an automatic typesetting machine company that grew to over $50,000, and ballooned once more after outright buying the rights to the machine. The technology was supposed to replace human typesetters, and in a way it did — its main competitor, Linotype, completely owned the market, leaving Twain broke.
Kim Basinger Wanted to Make Her Own Sundance
In 1989, she sank $20 million into the 400-person town of Braselton, Georgia in an attempt to populate it with movie theaters and turn it into a big film festival town. Two years later, she and her partners sold it for $1 million.
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