Celebrity business ventures can turn out to be money-making juggernauts like Kim Kardashian's SKIMS or Rihanna's Fenty Beauty. But for every roaring success, there are plenty of epic failures.

From flopped fashion lines to doomed restaurant ventures, read on to discover celebrity schemes that totally missed the mark. 

All dollar values in US dollars

In 1988, Kim Basinger snapped up the entire town of Braselton, Georgia for $20 million (the equivalent of $53m/£40m in today's money), hoping to turn it into a movie-themed tourist attraction. She really shouldn't have bothered.

The 1980s icon failed to realise her ambitious plan and ended up selling the town for a hugely marked-down $1 million ($2.1m/£1.6m today) in 1994. 

This trio of Hollywood stars were all smiles at the launch event for their Planet Hollywood chain of restaurants in 1991. Little did they know that their chain of eateries would go bankrupt twice, amassing colossal debts.

As of today, only four Planet Hollywood restaurants survive in America, down from a peak of over 100 in the mid-1990s.

Director Steven Spielberg's movies may have earned him millions of dollars, but the Beverly Hills restaurant he launched with Jeffrey Katzenberg in 1994 wasn't quite so lucrative.

A hit for a time, the nautical-themed eatery soon lost its lustre and shut down in 1999.

Wrestling star Hulk Hogan was knocked down when he invested in the fast food industry. His incredibly tacky Pastamania restaurant in the Mall of the Americas opened its doors in 1995, tempting diners with dishes including cheeseburger pasta and Hulkaroni and cheese.

Unimpressed, the crowds failed to flock, and the eatery went under within a year.

Wrestling bigwig Vince McMahon thought he'd cash in big time in 2000 when he formed XFL, a major off-season American football league.

McMahon hooked up with NBC to televise the games, but the ratings were dire, and the league was culled after just one season.

Naomi Campbell, Elle Macpherson, Claudia Schiffer, and Christy Turlington launched their Fashion Café chain in the mid-1990s. Branches in New York and London opened to much fanfare but were gone by 1999.

The cafés failed to pull in the diet-obsessed fashion crowd, and the supermodels' business partners ended up being arrested for fraud.

Britney Spears lost a pile of cash in 2002 when her Cajun-inspired New York restaurant Nyla went belly up after just six months.

Beset by bad reviews and health code violations, the restaurant was an unmitigated disaster from the get-go.

Former Chicago Bear Jim McMahon clearly hasn't heard the expression "once bitten, twice shy".

The NFL star opened his eponymous Chicago eatery in 1987, which went under after three years. Undeterred, McMahon tried again in 2002 with a steakhouse, and that too failed, closing its doors within a year.

Always the most sociable Rolling Stone, guitarist Ronnie Wood has lost money following two clubs going under. There was the nightclub Woody's On The Beach in Miami, Florida which saw a pantheon of famous names perform but closed its doors in 1989.

And there was the Harrington Club in London's South Kensington, a private member's club that opened in 1999 but closed in 2003, with Wood unable to recover any of the art and books he had lent to be displayed.

Kevin Costner teamed up with Jack Niklaus in 1997 to establish a golf-themed restaurant in Costa Mesa, California.

The eatery, which served hearty American fare, did well for a time but eventually became unprofitable, closing its doors forever in 2007.

You'd think that the hotel industry would run in her blood, but Nicky Hilton came unstuck in 2007 when she struck a deal to front her very own branded chain.

The first Nicky O Hotels, which were planned for Chicago and Miami, were cancelled before they even got off the drawing board.

Nicky's older sister, Paris, has had a taste of business failure too.

In 2008, the hotel industry heiress released a clothing collection under the Dollhouse label, which featured garish T-shirts emblazoned with her image. It was panned by critics and shoppers alike.

Though she's had her fair share of entrepreneurial success, Jennifer Lopez has two major business failures under her belt.

The A-list star's Madre's restaurant folded in 2008, and her Sweetface fashion line was discontinued a year later following disappointing sales.

Animal lover Natalie Portman thought she was doing the right thing when she collaborated with designer Té Casan on a vegan shoe line back in 2008, but while the actor should be applauded for sticking to her principles, she won't get any accolades for business acumen.

Overpriced and unappealing, the shoes didn't sell, and, within months, the business collapsed.

Rapping and producing hit records may come naturally to Jermaine Dupri, but operating a successful café evidently doesn't.

Launched in Atlanta in the summer of 2005, Dupri's eponymous cafe failed to turn a decent profit and closed in 2008.

Another major celebrity fashion line failure was reality star Heidi Montag's 2007 collaboration with Anchor Blue Retail on her Heidiwood fashion line.

The clothes and accessories failed to get customers to part with their cash, and the line was axed in 2008.

The Kardashian sisters have generated millions of dollars thanks to businesses they've set up or endorsed, but their venture into prepaid debit cards went down like a lead balloon.

The "Kardashian Kard" was ditched a month after its launch in November 2010 amid criticism over its astronomical fees.

The award-winning rapper has his fingers in many money-making pies, having established a glittering business empire with interests in fashion, real estate, sports teams, record labels, and beverages.

But it hasn't all been plain sailing. In 2010, Jay-Z lost millions on a luxury hotel investment in New York that came to nothing.

Making money in the fast food industry isn't easy, as Public Enemy rapper Flavor Flav discovered in 2011.

A joint effort with his business partner Nick Cimino, Flav's restaurant in Clinton, Iowa opened in January but was closed for good by April, and the hapless pair fell out amid accusations of mismanagement and poor cash flow. 

Former Major League baseball star Curt Schilling gambled the bulk of his life savings in 2006 on his online gaming start-up, 38 Studios, which he named after his jersey number.

Despite a $75 million ($117m/£87m in today's money) grant from the State of Rhode Island, Schilling's business failed spectacularly – out of cash and severely in debt, the company went bankrupt and shut down in 2012.

Lily Allen's foray into the fashion industry was unfortunate. The British singer teamed up with her half-sister Sarah Owen in 2010 to open Lucy in Disguise, their vintage clothing hire service in London's Covent Garden.

Following poor sales, the boutique moved to cheaper premises in Soho but ultimately went into liquidation in 2012.

Together with several other musicians, Fall Out Boy's Pete Wentz opened the Angels & Kings nightclub in New York in 2007.

Poorly managed, the club ended up attracting an underage crowd and was shut down by the authorities in 2012 for serving alcohol to minors.

In 2008, Eva Longoria launched the restaurant Beso in Los Angeles, but the business struggled and filed for bankruptcy in 2011.

She converted the Las Vegas restaurant into the family-friendly SHe steakhouse, but that fared just as badly. It shut down for good in 2014 after just two years of operation.

Beyoncé has a knack for making money, but the House of Deréon, the fashion line she set up with her mother Tina Knowles in 2006, was a business disaster.

Mocked for its gaudy designs and excessive prices, the line flopped and was quietly discontinued in 2012.

Pharrell Williams collaborated with drinks giant Diageo in 2011 to launch a liqueur called Qream with a Q aimed at "independent and successful women".

Sales of the tipple fell flat, and Williams sued Diageo in 2013 for failing to market the drink effectively.

Reality star and entrepreneur Kim Kardashian is now a billionaire thanks to business ventures like her SKIMS shapewear line and SKKN By Kim skincare collection. However, not all her side hustles have been so successful.

Kardashian launched an affordable jewellery line, Belle Noel, in collaboration with designer Pascal Mouawad back in 2011. Critics described the Egyptian-themed pieces (pictured) as gaudy, and the business shut up shop shortly after its inception.

Actress Blake Lively clearly assumed her lifestyle website would be a major success; after all, Gwyneth Paltrow's GOOP has done pretty well.

But Lively's Preserve website, which launched in 2014, remained online for only a year before it was canned.

In 2014, Canadian singer-songwriter Neil Young launched a successful Kickstarter campaign and garnered $6.2 million ($8.2m/£6.1m today) to fund his $400 ($530/£395 today) hi-res player and music service.

There was just one catch: PonoPlayer wasn't very good. The product didn't sell well, and the streaming service effectively bombed.

Less than two years after Rihanna launched her Fenty fashion label, it closed down in 2021. Rihanna was the first black woman to lead a fashion house under the luxury French LMVH brand.

However, critics slammed the price point of Fenty clothing and said the cost was unattainable for the singer's core fanbase. It's not all doom and gloom, though. Billionaire Rihanna continues to rake in millions from her Savage X Fenty lingerie line and her Fenty Beauty and Fenty Skin businesses.

F1 star Fernando Alonso launched his clothing brand Kimoa in 2017. However, the company failed to get off the grid and suffered losses of $3.2 million (£2.4m) in 2021. This led to 75% of the company being sold to US-based group Revolution Brands for $3 million (£2.2m), placing the company's valuation at a modest $4 million (£3m).

Despite its rocky start, Kimoa was given a second lease of life in 2023 when it announced a partnership with Alonso's F1 team, Aston Martin. The brand recently launched a 2024 collection in collaboration with Aston Martin, signalling a new chapter. 

Sean Stewart, the son of legendary rock star Rod Stewart, launched his streetwear brand Dirty Weekend in 2022. Failing to make waves in the fashion world, the ill-fated business has already been relaunched twice since then, according to inside sources.

Perhaps hoping that the third time is a charm, Sean has reportedly "cashed out" and blown through the inheritance he would have received on his father's death in a bid to save the failing venture.

Now discover the bankrupt billionaires who lost it all

Updated by Alice Cattley