Some Of The Worst Investments Made By Celebrities

#1 Jay-Z

Jay-Z definitely needs to stick to apparel and his music. His hotels in NYC were a huge bust. Back in 2007, the music mogul bought some land in Chelsea and built a 150,000 square foot luxury hotel. In 2008, construction was shut down due to lack of funding. His company defaulted on a $52 million loan and his partners gave the land back to the bank.

#2 William Shatner

Back when William Shatner became the face of Priceline, he requested stock options instead of monetary payments. Reports say his take from the deal is around $600 million, but Shatner clains he has not made that much. The official number may not be super big, but he definitely has made a pretty penny from this venture. But, in 2000 during the dot-com crisis, shares dropped down to $1.80 each but have rebounded since to around $300.

#3 Britney Spears

We all know Britney has had quite a few personal train wrecks over the years, but as far as business goes, her biggest fail was her Manhattan restaurant NYLA. It was a combo of New York and Louisiana style food. When it opened back in 2002 it mainly focused on Cajun dishes but the chef started incorporating and replacing dishes with Italian style eats. Not only did the reputation of the restaurant go down but it also had a slew of chronic health code violations. It closed after just six months.

#4 Kanye West

Hip hop recording artist Kanye West debuted two fashion lines at Paris Fashion Week in 2011 and 2012 to mixed reviews. His first fashion venture ever, Pastelle Clothing, was intended to be released in the Spring of 2006, however, after four years of development, the line was cancelled in 2009.

His second women’s fashion label, DW Kanye West, debuted at Paris Fashion Week in 2011, and though his star-studded audience included the Olsen Twins, Jeremy Scott, and Olivier Theyskens, the line was received poorly by critics including The Wall Street Journal, Harper’s Bazaar, The New York Times, and the International Herald Tribune.

#5 Curt Schilling

Curt Schilling is known for his love of video games. He launched an online gaming start up called 38 Studios. He put $30 million of his savings into it along with $75 million from the state of Rhode Island to build the offices and hire local workers, and it ended up being a huge failure. In 2012 they failed to make payroll and laid off almost 400 employees before declaring bankruptcy.

#6 Kevin Costner

Kevin Costner invested millions in two companies that focused on green technology and were inspired by the Exxon Valdez incident in 1989. He lost over $40 million. Now, the ill-fated companies he invested in back in the day may help to clean up the most recent oil spill in the Gulf. He went down to NOLA to demonstrate an oil spill cleanup machine that he started working on 15 years ago. He and the NOLA locals are very enthusiastic that it will be of some help.

#7 Jennifer Lopez

J-Lo is known for her entrepreneurship, but she is not the most successful one. Even though she is a hugely successful singer and actress, she still has much to learn before being a success in the restaurant and fashion business. Two of her clothing lines have stopped production, and her restaurant closed after only being in business six years.

#8 Hulk Hogan

Wrestling legend Hulk Hogan should really stick to what he knows. His fast food restaurant, Pastamania, went down in a blaze of shame in 1995 despite the backing of the then WWF. It closed down in less than a year.

#9 Mark Twain

Mark Twain has been called America’s first modern celebrity, so his bad investment should be no surprise. Mark Twain spent $150,000 to $300,000 (a massive amount of money back then) over 11 years during the late 19th century on a machine called the Paige Compositor. This was a typesetter that was said to be faster than standard Linotype. Unfortunately, the machine had more than 18,000 parts and needed constant care, so the business died.

#10 Bono

The U2 frontman is a managing director for the private media and entertainment equity firm Elevation Partners. After making a killing with investments in Yelp, Facebook and video game companies BioWare and Pandemic Studios, later investments in Palm ($460 million) and Forbes, Inc. ($300 million) turned into huge losses. Ultimately, Elevation’s return on those investments was only $25 million, which was enough to convince the website 24/7 Wall Street that Bono is “the worst investor in America.”

#11 Kevin Bacon and Kyra Sedgwick

Kevin Bacon and Kyra Sedgwick lost millions in a Ponzi scheme run by the notorious Bernie Madoff, Bacon did eventually speak out, once the list of victims started coming out, stating that he was looking for new projects to invest in since he had lost so much.

#12 Chamillionaire

Since his hit "Ridin" hit number one on the Billboard 100 and won Best Rap Video back in 2006, he has not been able to achieve any mainstream success. He did, however, invest in a string of auto dealerships and created his own music label.

In 2010, he defaulted on his 7500 square foot mansion in Houston because the home had become worthless and it was best for him to just eat the loss.

#13 Kim Basinger

Kim Basinger has perhaps made the most stupid purchase in celebrity history. She actually invested some $20 million in a town called Baselton in Georgia in hopes of turning it into a tourist hotspot. After her purchase, she struggled to manage her plans to realize her dream and resold it for just $1 million five years later and then filing for bankruptcy.

#14 Flavor Flav

We all know Flava Flav is not the brightest light bulb in the box. In an attempt to compete with Popeye's and KFC, he started his own chicken chain called "Flav's Fried Chicken." Due to some disputes with Flav and his partner, the chain never had a chance to take off the way it was planned. He did try to launch it on his own in Las Vegas and Michigan, but was very unsuccessful.

#15 The Kardashians

Known as Hollywood Royalty, this family has their hands in a little bit of everything and are quite successful for the most part. However, finance is not their strong suit. Their biggest fail was a prepaid Mastercard as it was jam packed with large and excessive fees which included a fee that ranged from $60- $100 activation fee. They pulled out of their partnership with Mastercard after less than a month and lost between $40 and $60 million over the whole thing.

#16 Oprah Winfrey

Though she won't openly admit it, but her OWN network channel is not off to the best start. She had hoped, since her "The Oprah Winfrey Show" was the highest rated talk show in history, that all of her fans would follow her media company. After just its first week, the channel lost almost 700,000 viewers and has suffered over $300 million in losses.

#17 Nicky Hilton

Nicky who is already an heiress to the very successful Hilton hotel line attempted to create a luxury hotel of her own in Miami. The hotel would have 95 luxury suites priced at $1000 per night. Unfortunately, the building she purchased was nothing but a huge headache with tons of issues. The project failed, and she filed for bankruptcy within a year of announcing her plans for the building. She was later sued by the contractor and the property was auctioned off.

#18 Burt Reynolds

During the 1970s, Burt Reynolds decided to open a restaurant chain called PoFolks in California, Florida, and Texas. By the late 1980s, he was out $15 million. His unfortunate divorce to Loni Anderson led him straight into bankruptcy. He was $10 million in debt, but the courts were nice enough to allow him to keep his $2.5 million mansion and his personal property that Anderson left behind.

#19 Natalie Portman

In a partnership with the New York City store Té Casa, Portman created a line of vegan friendly shoes which sold at a hefty $200 per pair. Due to a poor economic climate, her venture with Té Casa failed in under a year.

#20 Larry King

Larry King got himself caught up in an insurance scam that was flipping policies for profit. He gave up two policies that were worth $15 million but only made back a measly $1.4 million off the sale.