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20 Celebrities Who Dared To Change Their Careers But Some Plans Went Astray

Although statistics show that the average person switches careers five or six times during their lifetime, this is rarely the case with celebrities. After all, when you're so famous for something that you're internationally acclaimed (plus millions of followers on social accounts and priority for a celebrity ), it's a pretty safe place that you'll stick with for as long as you can.
Of course, that's not true for everyone.
Some famous people decide to entirely change their lives rather than just try out a new job. From Dwayne Johnson’s career shift from pro wrestler to Hollywood heavyweight to Drake’s transformation from an actor into a famous singer. They have proven that making a switch from one job to another can be the best decision for their career.
But...it doesn't always go so well. While some celebrities have great success in their new careers, others have less luck with reinvention and decided to nail their original jobs. So, take a look at the transformations of 20 stars below. If you know other stars who have made massive career pivots, let us know in the comments!

#1 Taylor Swift - successful reinvention

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Taylor Swift is a great example of musicians-turned singers. Her fifth album, "1989", marked a genre switch to synth-pop, which is different from her first four country albums. Her next two albums were also pop (albeit with influences from other genres like R&B and rock)… but she changed genres once again with "Folklore" and "Evermore", two indie-folk albums (still with pop and rock influences).

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Despite her success in her music career, Swift still broke into the acting field, but things did not go smoothly. Her first role was a brief appearance on CSI, and she then made appearances in the underappreciated films "Valentine's Day", "The Lorax", and "Cats".

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#2 Paris Hilton - failed reinvention

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Although she also did some modeling and rose to fame as a reality star with "The Simple Life", Paris Hilton's prominence in the media throughout the 2000s was mostly due to her wealthy socialite. She started various lucrative businesses, most notably a perfume line, but in 2006 she decided to try her hand at singing. In August of that year, her debut album "Paris" was released. In fact, her single "Love Is Blind" was a huge smash, peaking at number 18 on the Billboard Top 100.

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It was the only album Paris had ever released, but it received mostly mixed reviews (although she did release a few more singles). Recently, she has tried her hand at DJing, even DJing at Summerfest and Tomorrowland. She has a lot of success and makes $1 million every set, but she also has a lot of critics.

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In addition, Hilton also tried her hand at an acting career, landing cameo roles on a variety of programs like "The O.C." and "Supernatural", as well as playing the lead role in "House of Wax". She received a Razzie for her performance, and she hasn't had an acting role (although she has starred in documentaries, as a TV host, and as a reality celebrity) since 2010.

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#3 Garth Brooks - failed reinvention

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Garth Brooks is one of the most unusual examples. In 1999, Brooks, then a successful country musician, decided to create an alter persona called Chris Gaines to prepare for a proposed film called "The Lamb" about the murder of Gaines.

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The fictitious Gaines was a rock musician, and Garth performed as Gaines on "Saturday Night Live" and in a mockumentary for "Behind the Music". Before the publication of "The Lamb", Gaines released an album under the name Garth Brooks in...the Life of Chris Gaines. And "The Lamb" was completely discarded when the performance is not as expected.

#4 Dwayne Johnson - successful reinvention

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Back in the late ’90s, Dwayne "The Rock" Johnson was primarily recognized as a pro wrestler. However, in 1999, he started appearing in small roles in addition to wrestling (which he retired from in 2004, though he did later return). His first significant role was "The Mummy Returns" in 2001, and after that he proceeded to land parts in high-profile films, making his way onto the A-list thanks to his part in the "Fast & Furious", "Jumanji", and "DCEU" franchises as well as the Disney movie "Moana". According to Forbes, he was the highest-paid actor in 2022.

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#5 Hulk Hogan - failed reinvention

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Wrestler Hulk Hogan unsuccessfully switched to a new job. In the 1980s, he tried his hand at acting by playing a small part in "Rocky III". He also had appearances in a few TV Movies and sequels, including a cameo in "Gremlins 2", as well as short-lived TV series like "Thunder in Paradise". None of Hogan’s lead movie roles were well-reviewed. A member of Hulk Hogan and Wrestling Boot Band, Hogan also released an album in 1995 when he was a world heavyweight champion called Hulk Rules. The band did not release another album after the disc was heavily criticized. However, the album has become a bit of a cult hit due to its “so bad it’s good” status.

#6 John Cena - successful reinvention

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John Cena made his film debut in the 2006 film "The Marine", but it wasn't until he played the lead in "Trainwreck" that people started to take notice of him as an actor. Following that, he started working on more well-known projects, such as "The Suicide Squad" and an HBO spinoff series based on his character Peacemaker.

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#7 Kim Kardashian - failed reinvention

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In 2011, Kim Kardashian, who was already a popular socialite and reality celebrity, tried out a singing career by releasing the song "Jam (Turn It Up)." Kardashian later said she regretted recording the song. “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? Like, I don’t have a good voice,” she said in 2014.

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#8 Mark Wahlberg - successful reinvention

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Mark Wahlberg's career began in the early 1990s with the hip-hop group Marky Mark and the Funky Bunch, who had success and had a number of hit songs. After making his screen debut in 1994's "Renaissance Man", he shot to fame with 1997's "Boogie Nights". He has also received nominations for a few Academy Awards for his performances in "The Fighter" and "The Departed".

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#9 Shaq - failed reinvention

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Shaq is most renowned for being one of the all-time great basketball players, but he has dabbled in a number of other ventures. He started acting in movies in the 1990s, including "Kazaam" and "Steel". Both received negative reviews, and he has received three Razzie nominations. Despite this, he still makes the occasional appearance in films and TV shows, generally in a cameo or as himself.

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However, Shaq has had some success as a rapper. He contributed rap verses to one of Michael Jackson's albums, as well as four discs of his own, one of which included Jay-Z and Notorious B.I.G. He hasn't put out an album in more than 20 years, but he's started DJing.

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#10 Lady Gaga - successful reinvention

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In the middle of the 2010s, Lady Gaga decided to try her hand at acting after years of success as a pop performer. She began with "American Horror Story", which earned her a Golden Globe. Then, she made her feature film debut in "A Star Is Born", playing a struggling wannabe singer. She won an Oscar for the role she played in the movie "Shallow".

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She went on to star in House of Gucci, and has numerous other roles in the works.

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#11 Robert Downey Jr. - failed reinvention

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Robert Downey Jr. attempted to transition from acting into singing by releasing his debut album, "Futurist", in 2004. Although the album wasn't a total failure, reviews were mixed, and it was Downey Jr.’s only test drive into music. He had just started a movie career comeback and would later become famous for playing Tony Stark in the MCU.

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#12 Taylor Momsen - successful reinvention

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Taylor Momsen is one of those celebrities who transitions the opposite way - from movie star to music star. "How the Grinch Stole Christmas" gave Momsen her first significant part as Cindy Lou Who, and she also made appearances in other family movies including "Spy Kids 2". Additionally, she started appearing on "Gossip Girl" in 2007 as Jenny Humphrey. She played a lead role for three seasons, but her appearance in the fourth season was limited to a few episodes. After Season 4, she finally left the show.

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In 2009, she started her band, "Pretty Reckless", and in 2010, they issued their debut record. Since then, they have put out four albums, performed on tour with the Veronicas, Evanescence, Fall Out Boy, and Marilyn Manson, and had their music included in motion pictures and television shows.

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#13 Cindy Crawford - failed reinvention

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Cindy Crawford was an international star in the 1980s and became one of the few supermodels to dominate the fashion industry in the 1990s. But in the middle of the 1990s, she made the decision to experiment. In 1995, Crawford was featured in "Fair Game", a thriller movie with William Baldwin. The film received negative reviews, especially from those who criticized Crawford's performance. — one wrote, “One could scavenge the thesaurus to find synonyms for ‘awkward’ to describe Crawford’s performance,” and another wrote, “Crawford would be advised to keep her day job.”

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Up until the early 2000s, she had a few TV series only, but her film career was over by that point. Aside from music videos, a 2009 appearance on Wizards of Waverly Place, and a few appearances as herself, she hasn't gotten into acting since.

#14 Drake - successful reinvention

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If we're talking about actors-turned-singers, we really can't ignore Drake. He appeared as Aubrey Graham in the teen series "Degrassi: The Next Generation". In 2006, while he was filming on Degrassi, he released his first mixtapes. He produced two more copies in the late 2000s before releasing his full-length debut album in 2010, making him an even bigger star. Since then, he has been nominated for and won four Grammy Awards.

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#15 Addison Rae - failed reinvention

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Influencer Addison Rae recently tried her hand at singing. After being famous for her dances on TikTok, she decided to release the track "Obsessed" in 2021. She went on to perform it on "The Tonight Show Starring Jimmy Fallon". The song — and performance on Fallon — received negative reviews, and Rae hasn't spoken anything about the next album she had teased.

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She also made her feature debut with the rom-com "He's All That" in 2021. Even though the movie received negative reviews, Addison has signed a deal with Netflix, so it's doubtful that her fledgling acting career will end any time soon.

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#16 Diane Kruger - successful reinvention

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Diane Kruger transitioned successfully from modeling to acting. She booked ads and runway shows for several luxury brands during the 1990s, including Armani, Dior, and Burberry. She has also done magazine covers, including Vogue Paris. However, she turned to a film career and played major roles in "Troy and National Treasure" in the early 2000s. She received rave reviews for her performance in "Inglourious Basterds", arguably her most popular part to date.

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#17 Jane Fonda - successful reinvention

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Jane Fonda made her acting debut in the 1960 film "There Was a Little Girl", for which she received a Tony nomination. Over the course of her acting career, she won two Oscars and an Emmy. She unexpectedly switched her professional focus to exercise videos in 1982 with her 22 workout VHS tapes.

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She even successfully pivoted back into acting in the mid-2000s and just finished starring on Grace and Frankie (for which she was nominated for an Emmy).

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#18 Bo Burnham - successful reinvention

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Bo Burnham began her career as a teenager in the mid to late 2000s by creating comedic YouTube videos. He recorded his first comedy special in 2010 and is performing stand-up comedy. Burnham maintained his massive success as a comedian with even more exceptional records, but he also made the decision to do something entirely different when he wrote and directed the 2018 indie hit "Eighth Grade".

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He also began a movie career with his first dramatic role in the Oscar-nominated film "Promising Young Woman" in 2020.

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#19 Olivia Wilde - successful reinvention

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Since the 2000s, Olivia Wilde has enjoyed a lot of success as an actress. However, in the early 2010s, she turned to direct. At first, she only directed some MVs and short films. Then, in 2019, Wilde established herself as a filmmaker with the critically-acclaimed and financially successful Booksmart. In addition, she is the director of the upcoming film "Don’t Worry Darling" though it’s been mired in controversy.

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#20 Jordan Peele - successful reinvention

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Jordan Peele began a successful career in sketch comedy in the 2000s by appearing on Mad TV. In the 2010s, he co-created and starred in "Key & Peele". Similar to Burnham, Peele decided to try his hand at directing in the middle of the 2010s, but in a very different genre. His directorial debut, "Get Out", was well-received by critics and went on to become one of the most well-known contemporary horror movies. It launched Peele's career as a horror filmmaker, and since then, he has directed two other movies and produced a number of others.

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