1. Lindsay Lohan’s Greek Holiday Comes To An End

Actress Lindsay Lohan may know the movie world through and through, but when it came to the hotel industry, everything was “all Greek” to her. In 2016, the iconic Mean Girls star decided to shift her focus from acting to the hotelier industry, by opening several hotels and nightclubs across Greece.

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Lohan participated in a reality show based on her new career, Lindsay Lohan’s Beach Club, premiering in early 2019 on MTV. The show, like her hotel ventures, fell flat. Just a few short months after the television premiere, it was announced it wouldn’t return for another season, while Lohan’s Mykonos beach club was also sold. While the actress claims the business has simply relocated to Athens under the new name of Lohan Seaside, others remain unconvinced.

2. Jessica Biel Caught Fudging Numbers at Her Restaurant

Actress Jessica Biel’s idea of an upscale children’s restaurant seemed good…at first. Biel, along with several investors, opened the kid-friendly restaurant Au Fudge in 2016. Despite the restaurant’s prime location in West Hollywood, Au Fudge closed in 2018, allegedly over several complaints from employees. In 2017, Biel and other owners, were hit with a wage-theft lawsuit after it emerged that they were cheating employees out of mandatory breaks, and bathroom visits.

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The restaurant’s owners failed to pay employees thousands of dollars’ worth of tips, collected from the venue’s many private events. In the civil complaint, staff members demanded $430,100 in missing tips, $31,549 for missed breaks, and $1 million in “punitive damages”. It seems that Biel, who admitted that running a restaurant was “way harder than being a producer”, won’t be changing careers anytime soon.

3. Kim Kardashian’s Single Hits A Sour Note

Kim Kardashian, the most famous member of America’s favorite reality show family, decided to dabble in a possible career change when she recorded a single. In 2011, Kardashian released her dance single “Jam (Turn It Up)”. Although the song had been produced by respected music industry figure The-Dream, the song was highly criticized. The heavily auto-tuned song made the New York Daily News label her “the worst singer in the reality TV universe”.

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As for Kardashian, she admitted to Watch What Happens Live host Andy Cohen, “I don’t have a good voice.” While she said that she regretted recording the song, she did see the silver lining, saying “it was a fun experience”, and that the proceeds from the brief career change went to a cancer charity. The song received only 63,000 downloads, and never appeared on the Billboard radio charts, becoming just one outrageous moment for the Kardashian family.

4. Scarlett Johansson Proves Fans Are Just Not That Into Her Music

The Lost in Translation star has always been vocal about wanting to pursue a music career. While her acting skills are often met with praise, the star’s music has received very mixed reviews, leaving the actress to reconsider any possible career changes. Johansson revealed that she had always harbored goals to sing, and do musical theater, but that her voice was too deep for her to be cast.

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In 2008, Johansson released her first album, Anywhere I Lay My Head, a collection of Tom Waits covers. It sold slightly less than 20,000 copies. Johansson then released Break Up, a collaboration with singer Pete Yorn, in 2009. The album received mixed reviews with some calling the star’s voice “nothing special”. Johansson continues to explore her musical abilities by recording songs featured in two of her film’s soundtracks: Sing and The Jungle Book.

5. Britney Spears Acting Leaves Fans, and Critics, At A Crossroads

For fans of Britney Spears, it seems there is no limit to what the pop star can do. That was until a highly criticized role in the 2002 teen dramedy, Crossroads. The film revolved around three Southern teens, who find themselves taking a cross-country road trip. Although the film was written by Shonda Rhimes, creator of successful shows like Scandal and Grey’s Anatomy, critics ripped it apart.

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While it was considered a box-office success, movie critics criticized Spears’ performance. Critics called the movie “mindless drivel”, a “train wreck”, and that the film was “groaningly, achingly, embarrassingly bad”. As for the pop star’s performance? USA Today wrote that Spears “has no acting talent to speak of”. Since her unsuccessful career change to actress, Spears returned to the music industry, where she is considered one of the best-selling musicians of all time.

6. Jennifer Love Hewitt Becomes Famous in Japan

As one of the biggest stars of the ’90s and early 2000s, Jennifer Love Hewitt seemed to be everywhere. The actress had released several albums, in 1992, 1995, and 1996. Her first album, Love Songs, was released solely in Japan, where it became a hit. Her other two albums failed to gain attention in the United States, and she was dropped from her label. Then, in 2002, she released a pop-rock album called BareNaked.

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Critics at Rolling Stones gave the album two stars out of five, referring to the album as a “joke” and that Hewitt sounded like a “karaoke singer”. The album enjoyed a short-lived success on the American and Australian pop charts, but was quickly forgotten. Since her lukewarm foray into music, Hewitt enjoyed success as the star of the Lifetime drama The Client List, a major role on the CBS drama Criminal Minds, and the FOX police drama 9-1-1.

7. Neil Young’s Brief Career Change to Tech Titan

Hoping to create a music player that would play songs “as they first sound during recording sessions”, Canadian musician Neil Young, introduced his version of a digital media player called Pono. Founded through a Kickstarter campaign, Young and PonoMusic, released their product in 2015.

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The digital music player used “higher-resolution” audio, said to produce higher quality audio compared to “the compressed audio inferiority that MP3s offer”. Called a PonoPlayer, users could download music from an online store. Despite Young’s passionate drive to “rescue the art form that I’ve been practicing for the past 50 years”, Pono announced the device would be discontinued in 2017. In a blind test, users couldn’t differentiate between Pono’s alleged high-quality sounds with those played on an iPhone.

8. Smokey Robinson’s Line of Frozen Foods Fails To Heat Up

In 2006, soul music legend Smokey Robinson took a unique turn in his career when he decided to launch a line of frozen food entrées. Robinson wanted to offer a line of healthier versions of traditional comfort foods. He hoped that his frozen meals would be “as satisfying to the soul as my music has always been to my fans”.

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Robinson’s line, which included various gumbos, and red beans and rice, was sold in large supermarkets across the United States. Unfortunately, the line didn’t exactly heat up. In addition to low sales, the Motown star was sued for trademark infringement over his use of the phrase “Soul is in the Bowl”, which had been trademarked by a Southern chef. Despite generally positive reviews of the food, Robinson’s line has slowly disappeared from the supermarket shelves.

9. Bruce Willis’ Singing Career Change Leaves Fans Confused

Bruce Willis took a drastic career change away from music when he became the gun-toting action hero most fans know him as. But before that, the star released his first album, The Return of Bruno. The pop-blues record received generally good reviews, and his single “Respect Yourself” even reached #5 on the Billboard Hot 100. While some critics admired Willis’ harmonica playing skills and voice, others didn’t think his voice was powerful enough.

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After a less well-received reception of his second album, Willis returned to acting, starring in a variety of movies and television series. He has won a Golden Globe, two Emmy Awards, and starred on Broadway. While Willis continues to play music, mainly with his band The Accelerators, he has focused his creative energy into the movie industry.

10. Planet Hollywood Comes Crashing Down to Earth

Planet Hollywood sought to combine casual American fare with celebrity when it opened its first restaurant in 1991 in New York City. Fronted by stars like Arnold Schwarzenegger, Sylvester Stallone, Bruce Willis, Demi Moore, and Whoopi Goldberg, the restaurant quickly became a popular tourist destination, leading to the chain’s expansion across the world.

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By 1999, the restaurant was in deep debt, going from being worth close to $2 billion to just $40 million in less than a decade. Business analysts blamed a variety of factors, including overly ambitious expansion, difficulty getting repeat customers, and complaints over prices and quality. The company filed for bankruptcy twice, and eventually closed the majority of its locations. The chain has since partnered with the Wyndham Hotel Group, developing Planet Hollywood Resorts in popular international tourist destinations.

11. Mandy Moore Gets Tangled in an Unsuccessful Clothing Line

Before she was making viewers sob as Rebecca Pearson on the NBC drama This Is Us, Mandy Moore tried her hand at being a clothing designer. The singer-turned-actress launched her contemporary line in 2005, calling it Mblem. Close to 6 feet tall, Moore hoped to create a line geared towards taller women. Mblem was sold in upsale retailers such as Bloomingdale’s and Nordstrom, and had a legion of celebrity fans.

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Despite its popularity, the line was discontinued only a few years later. Although Mblem wasn’t the success she had envisioned, Moore’s interest in the world of fashion continues. In an interview with fashion magazine WWD, the actress hinted that issues between her and her partners were at the root of Mblem’s failure. Moore has since focused on acting, but hasn’t ruled out returning to fashion.

12. Clay Aiken’s Political Run

Like most political races, the second season of the reality show American Idol had the country strictly divided between contestants Clay Aiken and Ruben Studdard. Aiken eventually placed second to Studdard, but continued his music career through the release of several albums, a stint on Broadway, and several guest appearances on television. In 2014, Aiken decided on a sharp career change, pursuing his interest in politics by running for a seat in the United States House of Representatives.

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Having won the Democratic primaries, Aiken ran as the Democratic Party’s candidate for North Carolina’s 2nd congressional district. Despite losing, Aiken continues to be interested in the political world. While he has not ruled out running for office again, he has focused his interest in a politically themed podcast called “How the Heck Are We Gonna Get Along”.

13. Robert Downey Jr. Goes From Futurist to Iron Man

Before he was zipping up his Iron Man costume, Robert Downey Jr. was trying on a different identity: as a musician. The actor, who initially gained international fame with roles in movies like Weird Science and on the television show Ally McBeal, released his debut album The Futurist in 2004.

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The adult contemporary album, which consisted of eight original songs written by Downey and two covers, received mixed reviews. While many praised Downey’s voice and musical talent, some felt his lyrics were “obtuse”. Since the album’s release, Downey has gone on to enjoy huge success in the some of the highest-grossing films in history. While the Sherlock actor is proud of his musical contribution, he doesn’t believe he will record another album.

14. Fashion Café Gets More Than the Fashion Police Involved

Hoping to cash in on the popularity of themed eating establishments, Francesco and Tommaso Buti founded the Fashion Café in 1995. Fashion Café was fronted by some of fashion’s biggest stars: supermodels Elle Macpherson, Naomi Campbell, Christy Turlington, and Claudia Schiffer. Unfortunately, the curtain came down on the runway after the chain’s founders were arrested for fraud, bankruptcy, and money laundering.

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It was alleged that Tommaso and Francesco Buti stole close to $12 million from investors, which they used to fund their opulent lifestyle. In addition to problems arising from the founders, restaurant goers were displeased with the fashion-themed restaurant. One 1995 review said the venue was “as empty as a supermodel’s belly”, lacking in “dining sophistication”. However, this investment faux pas was quickly forgotten, and the supermodels involved have continued strutting on with their careers.

15. Kardashian Kredit Kard

Hoping to capitalize on their popularity with teens, the Kardashian sisters launched their version of a “Kredit Kard”, The Kardashian Prepaid MasterCard. The card, which was advertised as a “fast and convenient way to manage money”, was quickly criticized by a variety of political personalities and prominent figures in finance.

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Connecticut Attorney General Richard Blumenthal was one of the card’s biggest critics, saying that the card’s many fees were “outrageous”, and that it sent the “wrong lessons about managing money”. Further investigation into the card revealed an excessive amount of “high fees” and “predatory rates”. Cardholders would be charged for even the most basic account transactions. Sensing the outrage, it was later reported that the cardholders would receive refunds, and that the Kardashian sisters ended their participation in the card.

16. Heidi Montag Launches Heidiwood

In the early 2000s, reality television’s resident bad girl, Heidi Montag, went from drama instigator on The Hills to fashion creator with her line Heidiwood. Montag, in partnership with denim purveyor Anchor Blue, debuted the Heidiwood line in 2008. The reality star’s collection was scathingly criticized by fashion experts, who were appalled by what they considered overpriced “paper-thin”, “flimsy” clothing.

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The career change proved short-lived, as just one year later, Anchor Blue discontinued the line. The company stated that they were taking a “completely new style direction”, opting not to renew their contract with Montag. The fashion venture wasn’t her first foray into unfamiliar territory. In 2010, she released an equally unsuccessful album called Superficial. Today, Montag has since starred on a variety of reality television shows.

17. Natalie Portman’s Line of Vegan Shoes Gets Slaughtered By Critics

Actress Natalie Portman joined forces with shoe design company Te Casan to release an exclusive line of vegan footwear. Portman, a vegetarian for close to two decades, was inspired to create a cruelty-free line because she found it difficult to find shoes that were “beautiful and comfortable” yet simultaneously not made of animal products. Unfortunately, despite her noble inspiration for the line, the footwear was brutally criticized.

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The leather-free shoes began at close to $200, a price point many industry insiders felt was too high. In addition to being expensive, fashion critics slammed the line, calling the shoes “a bit lackluster and dated”. The poor reception of her shoe line may have had Portman reconsidering her career change as fashion designer. Portman has since returned to the world of film, restricting her experimental fashion to the red carpet.

18. Eva Longoria’s Bad Luck in the Restaurant Industry

Like her character on the television series Desperate Housewives, Eva Longoria’s time in the restaurant industry has been filled with drama. In 2008, the actress, along with celebrity chef Todd English, opened a restaurant called Beso. The restaurant was an initial success, but shut its doors just a few years later.

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Many speculated that the restaurant closed after it was sued after an alleged assault took place in the venue. The closing of Beso came four years after health inspectors forced Longoria to shut down her female-geared steakhouse, SHe. In 2011, Longoria and her partners filed for bankruptcy, owing $5.7 million in debt. While she may not have found success in the food industry, Longoria has ventured into other projects including producing, philanthropy, and political activism.

19. Flavor Flav’s Restaurant Dreams Go Up in Smoke

In 2011, rapper Flavor Flav took his love for fast food to the next level when he opened Flav’s Fried Chicken (FFC). The Clinton, Iowa-based establishment was founded by Flav and his business partner Nick Cimino. Flav hoped that the restaurant, which also used a “secret recipe” for fried chicken, would become a popular fast food chain.

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Unfortunately, Flav and Cimino’s relationship quickly dissolved. Flav accused his partner of mismanaging the restaurant. Employees were dragged into the dispute after it emerged that a mistake with a credit card machine resulted in unpaid salaries. Cimino accused the Public Enemy rapper of not knowing “anything about the restaurant business”, and of absenteeism. While the restaurant has shut their doors, fans of the rapper hope he’ll continue his love for cooking with another culinary venture.

20. Beyoncé’s House of Deréon Fails To Make Its Mark On the Fashion World

Beyoncé is one of the most recognizable pop stars in the world, but unfortunately, her star power hasn’t been able to translate into success as a fashion designer. In 2004, Beyoncé and her mother Tina Lawson launched a ready-to-wear fashion line called House of Deréon. The line was followed by a junior’s line, called simply Deréon. In 2008, their girl’s line received criticism when it unveiled what many perceived to be inappropriate advertisements.

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In 2012 it was announced that House of Deréon would be relaunched, and the junior line Deréon would be discontinued. Beyoncé then partnered with UK-based clothing company TopShop to create a line of athletic clothing called Ivy Park. While the line did well financially, many criticized the lack of diversity of the line’s models, and lack of sizing options.

21. Steven Spielberg’s Restaurant Goes Underwater

Director Steven Spielberg and former DreamWorks CEO Jeffrey Katzenberg are some of the most innovative minds in entertainment. Unfortunately, their creativity couldn’t cross over into the culinary industry. In 1994, the pair opened an underwater-themed restaurant called Dive! Shaped like a huge yellow submarine, it featured metal catwalks, fish tanks, pressure gauges, and even simulated “dives”. The restaurant focused on sub sandwiches, and their “sub-stantial salads”.

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Despite clever marketing and interesting décor, the sub restaurant’s Los Angeles and Las Vegas locations went under in 1999. Critics from the Zagat survey called the food from the eatery “mediocre” and pricey. Fortunately, the closure was far from sinking either of the partner’s careers, and both have stepped back onto dry land and back into the entertainment industry.

22. Lance Bass Says Bye Bye Bye To His Astronaut Dreams

Most children dream of becoming astronauts when they grow up. Few continue to consider it a realistic career goal. Having achieved pop stardom, it seemed that space goals didn’t seem that lofty for NSYNC member Lance Bass. He moved to Russia and began the rigorous training required for him to become certified by NASA and the Russian Space Program, to take part in flying on a Soyuz Space Capsule.

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The boy bander had planned on joining the TMA-1 voyage to the International Space Station. But his dreams came crashing down to earth when his financial sponsors backed out, causing him to lose his seat. Despite not being able to fulfill his space goals, Bass remains passionate about space exploration, and still believes he will travel to space.

23. Nicky Hilton Proves She Doesn’t Have the Hilton Touch

Nicky Hilton is the descendant of hospitality royalty. A great-granddaughter of hotel tycoon Conrad Hilton, the socialite once said: “I’ve been around hotels my whole life, and I know a good hotel when I see one.” In 2006, Hilton tried her hand at the family business when she planned to renovate two Miami buildings to create her own hotel, Nicky O.

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The heiress planned on launching Nicky O hotels across the United States, enlisting designers like Roberto Cavalli to bring an air of elegance to the project. Her hotelier dreams were cut short when Hilton was sued by her former partner for breaching her development contract. The lawsuit alleged Hilton failed to promote the hotels, misrepresented her experience in interior design, and more. The concept was scrapped.

24. Debbie Reynolds’ Bad Vegas Bet

Debbie Reynolds was one of Hollywood’s most beloved actresses and singers, captivating audiences through her roles in classic films like Singin’ in the Rain and How the West Was Won. Behind the scenes, Reynolds avidly collected film memorabilia. In 1992, she purchased the Clarion Hotel and Casino, renaming it the Debbie Reynolds Hollywood Hotel. Beyond hosting a casino, she hoped the hotel would house a museum dedicated to Hollywood history.

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The career change idea was a largely unsuccessful venture, fraught with allegations of mismanagement. These financial issues eventually forced the actress to sell the property and declare bankruptcy. It is believed that the financial hit caused Reynolds to auction off the majority of her precious memorabilia and realize that her dream of a Hollywood history museum would never come to fruition.

25. Britney Spears’ Restaurant Dreams Are Over in a New York Minute

Britney Spears has never shied away from embracing her Southern heritage. In 2002, the Louisiana native opened her first restaurant, Nyla: a combination of the abbreviations of New York and Louisiana. The upscale eatery was set to feature modern takes on Cajun cuisine classics, such as po’ boys and gumbo, served in a hip atmosphere.

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Just six months after opening, Spears “terminated her relationship” with the bayou brasserie, blaming mismanagement. In addition to issues with management, the restaurant was also slapped with several health-code violations. In a last bid to attract customers, they even changed the menu to feature Italian-inspired dishes, but the damage was done. Since that disastrous career change from “pop princess” to restaurant owner, Spears has returned to an industry she is much better acquainted with: music.

Sources: NBC News, Entrepreneur, Insider