24 Celebrities Who Tried and Failed To Start New Careers

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Some celebrities have successfully made the transition from singer to actor or reality star to clothing designer, but not all stars have been able to start new careers. For these celebrities, what might have initially seemed like a good side job ended up being a major career fail. For some, it nearly ended their careers.

Last updated: Dec. 3, 2020
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Britney Spears

Some singers have successfully transitioned into the acting world — including Jennifer Hudson, Justin Timberlake and Mandy Moore — but Britney Spears is not one of them. Spears’ 2002 cheesy road trip movie “Crossroads” was panned by critics and currently has an abysmal 14% rating on movie review site Rotten Tomatoes. “Britney Spears’ feature debut is curiously low-key and even sad,” Roger Ebert wrote in his review for The Chicago Sun-Times.

Spears never returned to acting, but she went on to release seven more albums after the movie tanked. Spears has been on an indefinite work hiatus since January 2019.

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Garth Brooks

Several country stars have transitioned into other genres of music — Taylor Swift has found a lot of success doing it — but Garth Brooks was not as successful when he tried to change not only genres but also identities with the introduction of his Aussie rock star alter ego, Chris Gaines. Brooks only released one album as Gaines, but it is considered one of the biggest album flops of all time. Entertainment Weekly said the album’s debut in 1999 “pretty much ended the career of one of music’s top-selling acts.”

And that’s true to some extent. After releasing “The Scarecrow” in 2001, Brooks didn’t release a new album again until 2013. However, his career is on the upswing again: Brooks is currently on tour and received iHeart Radio’s inaugural artist of the decade award in 2019.

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Kim Kardashian West

Business mogul and superstar Kim Kardashian West has used her reality fame to launch several successful businesses including a makeup line and a gaming app, but even she agrees that she should never have tried to make it as a singer. In 2011, Kardashian West released the single “Jam (Turn It Up),” which was criticized for being “generic” and overusing auto-tune. Her single sold only 14,000 downloads in its first five days of sales, which wasn’t enough for it to crack the Billboard Digital Songs chart.

Even though Kardashian West has since married successful rapper Kanye West, she has not tried to release any more music. During a 2014 interview with Andy Cohen, the “Keeping Up With the Kardashians” star admitted she probably shouldn’t have released the one song she did.

“It’s definitely a memory and it was a fun experience,” she said on “Watch What Happens Live.” “We gave the proceeds to a cancer organization. But if there’s one thing in life that I wish I didn’t do … I don’t like it when people kind of dabble into things they shouldn’t be. And that I don’t think I should have. Like, what gave me the right to think I could be a singer? I don’t have a good voice.”

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Bruce Willis

Bruce Willis had achieved success as an actor on the show “Moonlighting” when he decided to give singing a go. He released an album, “The Return of Bruno,” in 1987, though he released it under the name of his alter ego, Bruno Radolini. The album actually charted, making it to No. 14 on the Billboard 200 chart.

Shortly after the album’s release, Willis shot to new levels of fame as the star of “Die Hard” — but that didn’t stop him from releasing another album. In 1989 he put out “If It Don’t Kill You, It Just Makes You Stronger,” but that album failed to chart, and since then, Willis has stuck to acting. He has a few movies currently in the works.

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Scarlett Johansson

Scarlett Johansson took the leap from acting to singing in 2008. She had recorded a cover of “Summertime” by George Gershwin for a compilation album and was asked by the record label if she would consider recording a whole album, she told Interview.

“I’ve just had so many friends who would kill for that opportunity that I almost couldn’t pass it up,” she told the magazine. “I have always loved to sing.”

Johansson released an album of Tom Waits covers called “Anywhere I Lay My Head,” and it received mixed reviews. She went on to release a second album but seems to have put her singing dreams to bed since becoming a member of the Marvel Cinematic Universe.

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Hulk Hogan

Hulk Hogan attempted to make the transition from WWE star to restaurateur with the opening of Pastamania at Minneapolis’ Mall of America in 1995. However, not enough people wanted to eat “Hulk-Us” or “Hulk-a-Roos,” so the pasta eatery closed less than a year after it opened. The former pro wrestler currently owns two locations of Hogan’s Beach Shop, which sells all sorts of “Hulkabilia.”

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Blake Lively

Although Gwyneth Paltrow has been able to turn her Goop lifestyle website into an empire of its own, Blake Lively was not as fortunate when she made her own foray into the lifestyle space with her short-lived site Preserve. Lively launched Preserve in 2014 as a digital monthly magazine/e-commerce site/video blog with a focus on handmade artisan crafts.

“People want to get back to the magic of smaller, special and handmade,” she told Vogue in 2014 about why she had created the site. “People want things with meaning. I know that because I want that. This space doesn’t exist, so I’m creating it.” But in 2015, she announced that the site was shutting down, telling Vogue that “it never caught up to its original mission: It’s not making a difference in people’s lives, whether superficially or in a meaningful way.”

Even though Lively failed to launch the next Goop, she’s doing just fine. When not raising her children with superstar husband Ryan Reynolds, the former “Gossip Girl” actress is continuing to make movies and is set to star in the upcoming film “The Husband’s Secret,” based on the Liane Moriarty novel, Variety reported.

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Robert Downey Jr.

In 2004, “Iron Man” star Robert Downey Jr. released an adult contemporary album, “The Futurist.” At the time, Downey’s acting career was in somewhat of a slump — he had lost his job on “Ally McBeal” and his recent movie, “The Singing Detective,” had bombed at the box office, Uproxx reported.

Since then, Downey’s acting career has rebounded in a major way — he was one of the highest-paid celebrities of 2019 with $66 million in earnings for the year, Forbes reported. The same can’t be said for his singing career, which ended after the single album release.

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Michael Jordan

Michael Jordan is considered one of the greatest basketball players ever, but his athleticism hasn’t translated to other sports. In February 1994, Jordan signed a minor league contract with the Chicago White Sox; his batting average with the team was .202. After one season, he moved to the Scottsdale Scorpions of the Arizona Fall League, where his batting average was .252. According to Sports Illustrated, he called himself the team’s “worst player” and returned to the NBA in March 1995.

Fortunately for him, Jordan’s brief stint as a pro baseball player did not ruin his career in basketball. He went on to be named MVP two more times, in 1996 and 1998. Although Jordan retired in 2003, he continued to make millions from endorsement deals. He currently has a majority stake in the Charlotte Hornets and owns several restaurants and a car dealership.

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Lindsay Lohan

Lindsay Lohan showed off her singing chops in the movies “Freaky Friday” and “Confessions of a Teenage Drama Queen,” and then went on to release her own album, “Speak.” The album actually wasn’t a total failure — it peaked at No. 4 on the Billboard 200 chart. However, her follow-up album, “A Little More Personal (Raw),” only reached No. 20. She did release another single — “Bossy” — in 2008 but hasn’t returned to music since then.

Lohan has since transitioned into the nightlife industry, opening a beach club in Mykonos and a nightclub in Athens. She even scored an MTV reality show based around the Mykonos club, but the show was canceled after one season and the club appears to be closed as well, Page Six reported.

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Jennifer Love Hewitt

Actress Jennifer Love Hewitt has had success on both the big and small screen as the star of “I Know What You Did Last Summer” (1997), “Can’t Hardly Wait” (1998), “Ghost Whisperer” (2005-2010), “Criminal Minds” (2014-2015) and more, but her attempt to make it as a singer never quite took off. Hewitt has released four studio albums — “Let’s Go Bang” (1995), “Jennifer Love Hewitt” (1996), “Love Songs” (1998) and “BareNaked” (2002) — but none have placed on the U.S. Billboard charts. Her single “How Do I Deal” is her only charting release, peaking at No. 57 on Billboard’s Hot 100 Chart in 1999.

After “Criminal Minds” wrapped, Hewitt decided to step away from her Hollywood life to focus on her family. She returned to TV in 2018 and currently stars on the series “9-1-1.”

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Clay Aiken

Eleven years after he appeared as a contestant on “American Idol,” Clay Aiken attempted to make a transition into politics as a Congressional candidate for North Carolina. Aiken ran as a Democrat in a district that tends to vote Republican, so his loss was not surprising. Seemingly undeterred by the results, Aiken told Time in 2015 that he would consider running for office again. “It’s not something I’m ruling out,” he said. “I think it’ll happen.”

Aiken recently returned to music, releasing a cover of “O Holy Night” with his former “Idol” rival Ruben Studdard in November 2019.

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It seems hard to believe that Beyoncé ever took a misstep in her career, but even Queen Bey sometimes makes mistakes. In 2004, Beyoncé and her mom Tina Knowles launched House of Deréon, a junior’s clothing line “where entertainment and fashion merge seamlessly,” according to the brand’s Facebook page. Despite its star backing, the fashion brand folded in 2012.

The failure of her fashion design career did not hurt Beyoncé’s career overall, and she’s since even found success in fashion despite her rocky start in the industry. The megastar launched her Ivy Park activewear line in March 2016, and it’s currently sold in stores across the world.

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Emma Roberts

Before she was a major film and television star, Emma Roberts was a teen actress on the Nickelodeon show “Unfabulous.” Roberts played a singer on the show and decided to take her own chance at being a singer in real life when she recorded an album in 2005. However, Roberts’ musical career was short-lived. She only put out the one album and said during a 2009 interview with Parade that she would not be returning to singing.

“My musical career is indefinitely on hold,” she said. “I don’t like people who become like ‘actor slash singer.’ I think people should be one or the other because usually, you’re not going to be great at both.”

Her decision to focus solely on acting seems to have paid off, as she’s become a household name as an actress. Roberts starred in “Scream Queens” and “American Horror Story,” and is slated to appear in several upcoming films.

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Lance Bass

After achieving astronomical success as a member of the boy band ‘N Sync, Lance Bass decided he wanted to actually become an astronaut. In 2002, Bass underwent training to become the youngest person in space. He was slated to spend a week aboard the International Space Station as a guest of Russia, but his plans never actually took off. A month before the space flight was leaving, the Russian Space Agency announced that Bass would not be on the flight, as he had failed to raise the $20 million fare.

Even though Bass hasn’t yet made it to space, the singer told Business Insider in December 2016 that he hasn’t given up on his dreams to travel to the final frontier. “There’s no specific date, but there are plans for me to go,” he said.

Bass is currently the host of “The Daily Popcast With Lance Bass” and is a co-owner of the restaurant Rocco’s WeHo in West Hollywood, California.

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Heidi Montag

“The Hills” star Heidi Montag has tried to extend her 15 minutes of reality fame into other careers but has been unsuccessful. In 2007, she launched her Heidiwood clothing line, but it was discontinued just a year later. Montag abandoned her fashion designer career and instead focused her efforts on becoming a pop star. In 2010, she released her album “Superficial,” the product of three years of work and nearly $2 million of her own money. Although Montag was confident that the album would be successful — so confident that she went broke making it — it sold less than 1,000 copies.

After she failed to be successful in other careers, Montag returned to reality TV. She has appeared on “Celebrity Wife Swap,” “Marriage Boot Camp: Reality Stars,” “Celebrity Big Brother” and, most recently, “The Hills” reboot, “The Hills: New Beginnings.”

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Ben Higgins

In July 2016, former “Bachelor” Ben Higgins decided to run as a Republican for a seat in the Colorado House of Representatives. However, just two days after the news broke, he withdrew his candidacy. “Due to unforeseen circumstances, I will not be able to move forward as a candidate,” he said in a statement obtained by People.

In October 2016, Higgins said he had not given up his political career ambitions, and told Entertainment Tonight he was “excited to pursue that in the future” — though he has not announced any official plans to run for office.

Higgins is now the co-founder of Generous and sits on the board of Humanity and Hope United, a nonprofit that aims to serve underprivileged villages in Honduras. He also co-hosts “The Ben & Ashley I Almost Famous Podcast” with fellow “Bachelor” alum Ashley Iaconetti.

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Flavor Flav

Flavor Flav successfully transitioned from rap star to reality star — his show “Flavor of Love” was a hit for VH1. However, his turn as a restaurateur has been a failure four times over. Flav has opened four different locations of his fried chicken restaurant over the years, and all four have closed, Eater reported.

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Mandy Moore

Mandy Moore first gained fame as a singer, then successfully transitioned into the world of acting, but not all of her career endeavors have been successful. Moore launched a contemporary clothing line called Mblem in 2005, and in 2009, she shut it down.

“I love the fashion world. I’m fascinated by it. I’m humbled by it,” she told WWD at the time. “If I were to dip my toe back in there, it would have to be the right situation: a great partnership that could represent a true reflection of me and my ideas, and that wasn’t happening. So next go-round, that needs to be top of the list.”

Even though she failed as a designer, Moore has still achieved plenty of success. She currently stars on “This Is Us” and earned a Golden Globe nomination for her role.

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Steven Spielberg

Steven Spielberg is the highest-grossing movie director of all time, with his films earning a lifetime gross of $4.5 billion, according to Box Office Mojo. But Spielberg’s directorial eye couldn’t save his themed restaurants from sinking. In the mid-1990s, the director partnered with Dreamworks CEO Jeff Katzenberg to open two locations of Dive!, a submarine-themed restaurant that specialized in sub sandwiches — the restaurant even had a deep-sea dive simulation every 30 minutes. Although Dive! originally had lines out the door, it was panned by critics for having mediocre, overpriced food. In 1999, both the Los Angeles and Las Vegas locations closed.

Despite his failed foray into the restaurant business, Spielberg continues to achieve big-screen success. His movie “West Side Story” is due out later this year, and he will also be directing the fifth “Indiana Jones” movie, due out in 2021.

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Naomi Campbell

Supermodel Naomi Campbell has appeared in a number of music videos, but she failed to successfully cross over to be a musician herself. Campbell released her one and only album, “Baby Woman,” in 1984. It was panned by critics and only sold 175 copies in the first two weeks of its release, The Guardian reported.

Although her music career never took off, Campbell had a very successful modeling career to fall back on — and she’s still modeling three decades later.

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Kobe Bryant

The late, great Kobe Bryant played 20 seasons for the NBA — and he also had a short-lived rap career. In 2000, Bryant released his first and only single, “K.O.B.E.” He performed the song during the 2000 All-Star Weekend, along with Tyra Banks, and it was not well-received. The accompanying music video was never released, and Sony dropped him from its label. Bryant then co-founded his own independent label, Head High Entertainment, but that folded within a year, Grantland reported.

Fortunately, he had his basketball career to fall back on. Bryant went on to play 16 more seasons with the L.A. Lakers and was MVP for the 2007-08 season.

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Natalie Portman

Natalie Portman had a brief stint as a shoe designer. The actress teamed up with designer-shoe boutique Te Casan to launch a line of vegan footwear in February 2008, but just a few months later — in November of that same year — the company folded and the store closed for good.

Portman’s acting career is still going strong, with several films set to be released in the coming years.

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Tyra Banks

Tyra Banks has transitioned from supermodel to TV host to media mogul, but the one career she couldn’t quite get off the ground was singer. Although she released her first and only single — “Shake Ya Body” — in 2004, Banks said it was a move that was six years in the making.

“After retiring from modeling, the only way I thought I could continue to work that stage that I loved so much was I had to sing in order to do it,” she told Entertainment Weekly. “If my voice was amazing, I would’ve been a huge pop star. But my voice was just decent, and that’s not good enough to transition from being a model.”

But it wasn’t a total loss. Banks told the magazine that her failed singing career led her to focus more on launching her talk show, “The Tyra Banks Show,” which ran from 2005 to 2011. Banks’ latest endeavor is an interactive modeling-themed attraction, ModelLand, which will be opening in Santa Monica, California.

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