20 Celebrities Who Failed Miserably Before Finding Success

In the words of that timeless purveyor of wisdom, Yoda, “the greatest teacher, failure is.” When we see people who have achieved fame and fortune reaching the upper echelons of their chosen field, we sigh enviously at their good fortune and wonder how they got so lucky.

However, few people have achieved such success without hitting some major stumbling blocks along the way. Consider the following superstars, all of whom faced setbacks that might easily have convinced them to quit.


20. Henry Cavill

Credit: Gage Skidmore

There was a time when British actor Henry Cavill was considered one of the unluckiest guys in the business. In 2004, Cavill was cast as Superman only for the film to get cancelled; he was one of the top contenders for the next James Bond, but missed out to Daniel Craig; and he lost out on two major roles in Harry Potter and Twilight, both to Robert Pattinson.

After such a string of misfortune, Cavill could easily have gotten despondent. However, he hung in there, and eventually he got to play Superman in 2013’s Man of Steel, followed by Batman V Superman and Justice League. Cavill has since enjoyed further success with Mission: Impossible – Fallout and Netflix series The Witcher.

19. Lisa Kudrow

In the early 90s, Lisa Kudrow was one among the countless young actresses trying to get make a name for herself. In 1993, she landed the role which looked certain to be her big break: Roz Doyle on Cheers spin-off Frasier. However, three days into production on the pilot episode Kudrow was fired and replaced by Peri Gilpin.

Kudrow has since admitted she “wasn’t right for the part,” but her dismissal was still a shock to the system that left her afraid that her career would fail. Fate had other plans, though, and within a year she was cast as Phoebe Buffay on Friends, which proved to be the most popular sitcom of the 1990s and made her a huge star.

18. Chris Pratt

Plenty of big-name actors know from an early age that it’s the path they want to follow, but Chris Pratt admits he had no idea what he wanted to do with his life when he was young. He spent many aimless years struggling to get by, and eventually wound up homeless in Hawaii, living out of his van.

Finally, Pratt experienced the dream of every aspiring actor: he was discovered whilst waiting tables in a restaurant and offered a small film role. Despite his complete lack of experience, this was enough to get Pratt on his way to a hugely successful career, taking him to TV’s Parks and Recreation and eventually to blockbuster roles in the Guardians of the Galaxy and Jurassic World movies.

17. Vera Wang

Credit: Christopher Peterson via Wikimedia Commons

Back in the late 1960s, Vera Wang was a successful young figure skater with her sights set on Olympic glory. Unfortunately, she failed to make the cut for the US Olympic team, which was naturally a devastating blow for the ambitious young woman. Wang realised she needed to find a new path to follow.

The death of her Olympic dream led to Wang instead pursuing work in the fashion industry. She went on to become the youngest ever editor of Vogue magazine and enjoyed massive success as a dress designer, her work including many celebrity wedding gowns. As of 2022, Wang’s estimated net worth is $650 million.

16. Oprah Winfrey

Credit: Milwaukee via Wikimedia Commons

After a very humble upbringing, Oprah Winfrey found her first on-camera job in television as a news anchor in Baltimore. She held this position for several months before she was fired, reportedly being informed by a producer that she was “unfit for television news.” Naturally, Winfrey says this “shook me to my core.”

Even so, Winfrey refused to let this keep her from pursuing TV success. Relocating to Chicago, she landed a morning talk show which would soon be renamed The Oprah Winfrey Show. Soon Winfrey was the biggest name in talk shows and branched out into other fields including acting, writing and business. Today, she has a net worth of over $2.6 billion.

15. Robert Downey Jr.

Credit: Gage Skidmore

After a brief stint on TV’s Saturday Night Live, Robert Downey Jr. broke into film in the mid-80s. Alas, his career was soon derailed by his personal problems, in particular his addiction issues. This reached a head by the late 90s, as Downey’s inability to stay clean resulted in numerous arrests, and lost him jobs.

By the early 2000s, Downey looked unlikely to ever get hired in Hollywood again. However, he gradually worked his way back up through small roles and independent films before the fledgling Marvel Studios cast him in the lead role of their first feature, 2008’s Iron Man. The rest is history: Downey enjoyed a meteoric revival, becoming one of the best-loved and highest-paid actors in the world.

14. Sylvester Stallone

Credit: Michael Schilling

Sylvester Stallone started out as an actor in the late 60s. He had virtually no success to begin with, and with no other job offers he wound up making his screen debut in a sexploitation film. At one point Stallone was so strapped for cash, he sold his dog for $40 in order to buy food.

Eventually Stallone was able to turn things around, selling his original screenplay Rocky on the condition that he be allowed to play the lead role. This put him on his way to a very successful career as an actor, writer and director, from which he is believed to have earned upwards of $300 million. Oh, and he bought the dog back.

13. Stephen King

Credit: Mario Tama/Getty Images

Back in the early 70s, Stephen King was a teacher with aspirations of becoming a full-time writer. Unfortunately, he had no faith in his first novel Carrie, and wanted to throw it out completely until his wife persuaded him not to. King’s first experiences with publishers did nothing to bolster his confidence: he received no less than 30 rejections.

However, once Carrie was finally published by Doubleday in 1974, it sold well and had largely positive reviews. Two years later, the movie adaptation of Carrie was a huge hit, which massively boosted interest in the writer. Soon thereafter, King became one of the most prolific and popular authors of all time, selling over 350 million books and inspiring more than 85 film and TV adaptations of his writing.

12. Lady Gaga

Credit: proacguy1 via Flickr

In 2006, Lady Gaga thought she had it made when she signed with Def Jam, the New York record label best known for hip hop. If you think the Poker Face singer-songwriter seems an odd fit there, you’re not alone: after only three months her contract was terminated as the bosses felt she was wrong for the label.

Getting dropped by a big-time record label is hardly any artist’s dream scenario, but Lady Gaga took it as an opportunity to learn, grow and develop her act. She’s since sold over 124 million records, won 13 Grammy Awards and also launched a successful acting career. As of 2022 her estimated net worth is $300 million.

11. Jim Carrey

Jim Carrey may have become one of the biggest names in comedy in the 90s, but things weren’t so rosy for the Canadian funnyman when he started out. Carrey scraped by doing movie and TV bit parts for years, whilst auditioning twice to join the cast of Saturday Night Live – only to be rejected on both occasions.

Carrey kept it up, however, eventually joining the cast of TV comedy series In Living Color before skyrocketing to big-screen fame with Ace Ventura: Pet Detective, The Mask and Dumb and Dumber. He quickly became a highly paid superstar, commanding huge salaries: his 2008 film Yes Man alone earned Carrey a reported $35 million.

10. JK Rowling

Credit: Daniel Ogren Photography

Today, J.K Rowling is renowned as one of the biggest-selling authors of all time. Her series of seven novels about the young wizard Harry Potter have sold 500 million copies worldwide, spawning a blockbuster film franchise and a slew of merchandising and landing Rowling with an estimated personal fortune of £820 million (just over $1 billion).

This is quite the about-face from Rowling’s humble beginnings. Following a failed marriage, she was a single mother struggling to get by on meagre government benefits whilst she was writing her first novel, Harry Potter and the Philosopher’s Stone. Worse yet, once she submitted the book to publishers it was rejected twelve times before Bloomsbury said yes.

9. Gal Gadot

After winning Miss Israel, serving in the military and working as a model, Gal Gadot headed to Hollywood to pursue a movie career. Yet despite making three appearances in the Fast & Furious series, Gadot found job offers were few and far between, and she was on the cusp of throwing in the towel and going home to Israel.

It’s just as well she didn’t, as in 2013 Gadot nailed the audition for the key role of Wonder Woman in Batman V Superman. Despite initial doubts from fans, Gadot’s performance won over audiences everywhere, and she made an even bigger splash with the first Wonder Woman solo movie in 2017. She’s since gone on to enjoy more success as a major leading lady.

8. Bill Gates

Credit: Michael Loccisano/Getty Images

Few names are quite so synonymous with wealth and success in industry as Bill Gates, the founder of groundbreaking computer company Microsoft. Gates didn’t become one of the highest-earning men in the history of the world overnight, of course; there were plenty of times he seemed bound to fail.

Gates’ first business, Traf-O-Data, was an outright failure. Even when Microsoft proved a roaring success, Gates took his eye off the ball a few times allowing Google and Apple to overtake him. That said, when you’ve got an estimated net worth of $125 billion, some minor slip-ups can be overlooked.

7. Katharine Hepburn

Back in the early days of cinema, Katharine Hepburn was one of the first major Hollywood leading ladies. Things didn’t look so great for Hepburn at first, however. In 1938 after she’d been in the business a decade, her contract with studio RKO was discontinued as the actress was deemed ‘box office poison.’

Little did they know how things would change. Hepburn became possibly the single most esteemed screen actress of all time, headlining scores of hits and winning the Best Actress Oscar four times (a record which stands to this day) between the 30s and the 80s.

6. Halle Berry

Credit: Matt Winkelmeyer/Getty Images

After competing in beauty pageants in her teens (including becoming the first African-American contender for Miss World), Halle Berry was 23 when she moved to New York to pursue an acting career. It didn’t come easily. Berry couldn’t find work and was soon so hard-up she had to move into a homeless shelter.

While her career picked up, Berry faced another major setback when she was diagnosed with type one diabetes. She refused to let this stop her, and worked her way up to becoming one of the most successful actresses of her generation, as well as the first (and to date only) African-American to be awarded the Best Actress Oscar.

5. Eminem

Credit: Dimitrios Kambouris/Getty Images for The Rock and Roll Hall of Fame

Back in the 90s, the idea that a white rapper could be taken seriously was considered laughable by most. As such, when Marshall Mathers first attempted to break into the field, he had to struggle to be accepted. Nor was this the only struggle to future Eminem had to endure.

Coming from lower-working class beginnings, Mathers was bullied as a child, once being beaten up so badly he went into a coma aged just nine. In the years since he’s also struggled with addiction issues and troubled relationships. Nonetheless, as Eminem he became one of the most acclaimed, highest-selling hip hop artists ever, breaking down racial barriers in the genre.

4. Walt Disney

Credit: Hulton Archive/Getty Images

It’s hard to imagine what popular culture today would look like were it not for Walt Disney. On top of being a pioneer of animation, Disney also revolutionised tourism with his theme parks, and established a corporation that dominates the entertainment industry today. How different things could have been.

Disney was fired from his first job as an animator on the grounds that he “lacked imagination and had no ideas.” Furthermore, his flagship character Mickey Mouse was reportedly turned down over 300 times before Disney was finally given the go-ahead to introduce the character in 1928’s classic cartoon short Steamboat Willie.

3. Steven Spielberg

Credit: Frazer Harrison/Getty Images

Back when Steven Spielberg was a young film enthusiast with dreams of becoming a director himself, he did what anyone in his position would do and apply to film school. However, his chosen school, University of Southern California, rejected Spielberg’s application – not once, not twice, but three times.

Ultimately, Spielberg was accepted to California State University Long Beach, but he soon dropped out after finding work at Universal Studios. This worked out well for him, as within a decade Universal hired Spielberg to direct Jaws, one of many massive blockbusters he would direct in his legendary career.

2. Michael Jordan

Credit: Mike Powell /Allsport via Getty Images

Michael Jordan changed the face of basketball when he rose to stardom in the sport in the 1980s. Not everyone saw this coming, however, not least the coach for Jordan’s high school varsity basketball team, who cut the young up-and-comer from the team.

While this kind of disappointment would deter many from pursuing their chosen field, Jordan has since said the experience only strengthened his reserve, and helped him realise he still had a way to go. His game did indeed improve, and he’s still considered one of the greatest players the sport has ever seen.

1. Elvis Presley

Credit: Michael Ochs Archives/Getty Images

When Elvis Presley first expressed an interest in music, he wasn’t given much cause for confidence. Coming from a poor family, he couldn’t afford the best instructors, and his high school music teacher told him he couldn’t sing. This left the young Presley so nervous and insecure that he couldn’t bring himself to sing in front of anyone.

Nonetheless, he stuck it out, and even as he made his first steps into the music business he faced rejection, failing two auditions to sing with bands. Yet as Presley continued to perform, his confidence on stage increased and he developed his own distinctive, revolutionary style of singing and performing which changed the face of music and saw him dubbed the King of Rock ‘n’ Roll.