Biggest Failed Celebrity-Owned Businesses

Even the most successful celebrities don't always strike gold.

Celebrities often venture into other businesses, hoping to leverage their fame into entrepreneurial success. However, not every venture becomes a triumph. These famous failures shed light on the challenges and setbacks that even the most prominent names face in the business world.

From fashion mishaps to restaurant missteps, these stories offer a glimpse into the less glamorous side of celebrity entrepreneurship.

Neil Young’s Pono Player Gets Passed Over

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Established in 2011 and heralded by legendary musician Neil Young as the next best thing in music with its enhancement of the the digital listening experience, Pono was set to rival and even outshine the iPod. The PonoMusic Store, a platform associated with the $400 player, aimed to deliver a superior quality of music.

Aside from its weird triangular design (which wasn’t easy to carry around like an iPod), critics found that the average user couldn’t tell the difference between what was played on a PonoPlayer vs. a supposedly inferior MP3 file. Young declared the official demise of the PonoPlayer in 2017.

Supermodels’ Fashion Cafe Fizzles

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The ’90s were the heydey of themed restaurants, when places like the Hard Rock Cafe, Dive and Planet Hollywood were at their peak. So, what better than a restaurant based around high fashion?

Supermodels Naomi Campbell, Christy Turlington, Claudia Schiffer and Elle MacPherson were the faces of the Fashion Cafe, which launched its flagship site in New York in 1995. (A total of eight locations were open worldwide.) The models were offered $50,000 to $100,000 for each personal appearance made at a restaurant opening, coupled with a share of the chain’s forthcoming profits, by brothers/entrepreneurs Tommaso and Francesco Buti.

But it was not meant to be. Both siblings were indicted on over 50 federal charges each, including fraud, money laundering and conspiracy. Federal authorities alleged that the Buti’s deceived Fashion Cafe investors by falsely claiming personal financial investment in the venture, while diverting funds into their own pockets.

Neither brother ever faced prosecution; both fled to their home country of Italy and were never extradited to the U.S.

Jessica Simpson’s Beauty Blunder

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Before she was a billionaire fashionista, singer Jessica Simpson ventured into the cosmetics industry with her brand Dessert Beauty in 2004, offering a range of flavored beauty products.

The line sparked controversy due to the sexualized marketing of its edible items, leading to legal disputes. Both Simpson and Sephora also faced lawsuits from the line’s manufacturers concerning unpaid profits. Within just a few months, Dessert Beauty was discontinued.

Before Yeezy, There Was Pastelle

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We know Kanye West blew up his Yeezy business relationship with Adidas by saying some incredibly offensive things in recent years, but it isn’t the first time his actions caused one of his business to fail.

In 2009, he created the fashion line Pastelle, which faced immediate challenges when images of the clothes surfaced online. Just as soon as they leaked, the business folded. Right before this setback, Ye’s public image suffered a blow when he interrupted Taylor Swift’s acceptance speech at the MTV Video Music Awards. Many speculate that this incident played a role in the demise of his fashion line. However, rumor has it that’s he’s bringing the line back in 2024.

Rihanna’s Fenty Fashion Fail

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RiRi has become a billionaire through beauty lines Fenty Beauty and Fenty Skin, as well as her lingerie collection, Savage X Fenty.

However, the Fenty fashion label, launched in 2019, was not nearly as successful. Operating under the LVMH group (which owns several high-end brands, including Louis Vuitton and Christian Dior), the label encountered difficulties through the COVID-19 pandemic and the steep pricing of the pieces. The label was finally discontinued in 2021.

Flavor Flav’s Fried Chicken Flop

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Public Enemy’s Flavor Flav dreamed of opening a fried chicken chain to rival KFC and Popeyes, and his first restaurant broke ground in Clinton, Iowa in 2011. Branded as “Flav’s Fried Chicken,” the establishment faced challenges from the get-go, as Flav and his co-founder/partner weren’t on the same page.

Flavor Flav persisted and sought to establish solo-owned franchises in Las Vegas and Michigan. Unfortunately, however, he just couldn’t get a foothold in fried chicken.

Kim Basinger’s Small Town Troubles

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Georgia native and “L.A. Confidential” star Kim Basinger joined forces with investors to buy the small town of Braselton for $20 million in 1989. The 1,750 acre town, home to about 400 residents, was envisioned as a potential tourist attraction with plans for movie studios and a film festival.

Regrettably, Basinger faced challenges in making her dream of the growing the town a reality. Struggling with personal financial difficulties, she sold Braselton in 1993 for a mere $1 million.

Braselton, however, persists. As of 2020, its population has grown to a considerable 13,403.

Natalie Portman’s Shoe Shambles

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Passionate about animal rights, Natalie Portman created a vegan shoe line in 2008. She joined forces with designer Te Casan to introduce a cruelty-free footwear collection.

While the shoes were pretty, many customers found the $200 price point a little too steep. By the end of that year, the Natalie Portman Collection for Te Casan ceased operations due to declining sales.

Nicky Hilton’s Hotel Is a Horrorshow

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You would think a Hilton would have the hotel business dialed in but that wasn’t the case when Nicky Hilton (sister to Paris) decided her venture and her famous family’s would be one and the same.

In 2006, she took part in planning a lavish 94-room hotel on Miami’s Ocean Drive, with a second location earmarked for Chicago. Italian fashion designer Roberto Cavalli was enlisted to design the hotel suites.

Originally intended to coincide with the 2007 Super Bowl in Miami, the project faced persistent delays and never saw a grand opening. The business filed for bankruptcy protection in 2007 and Hilton found herself in a lawsuit initiated by the hotel’s developer, who alleged that she failed to fulfill her obligations under the agreement.

Ultimately, the Miami property went up for auction and the Chicago project was abandoned.

Trump’s Shuttle Airlines Crashes and Burns

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Trump’s bankruptcies could be their own separate list, but did you know that he once had his own airline? In the early 1990s, he rebranded Eastern Air Lines’ shuttle as the Trump Shuttle. However, this venture quickly proved unsuccessful — it lost $125 million within just 18 months.

Trump’s unfounded attacks on competitor Pan Am’s safety procedures and maintenance practices also didn’t help. Additionally, the escalating price of oil as a consequence of the Iraqi invasion of Kuwait further contributed to the airline’s demise. By 1992, Trump Airlines was no more.