15 Celebrities Who Struggled More Than You In Their 20s

The decade that is your 20s is no doubt an exciting and bizarre time. But, whilst it might be the best time of our lives it is often the most difficult, confusing and heartbreaking. We are supposed to find a career in a world where there are more graduates but less job opportunities. We are bombarded with so much choice and so many different life pathways, it’s often difficult to know which one to take. And if we do take the right pathway, we’re supposed we feel the pressure to be successful from the get-go. Meanwhile, we’re bombarded with other people’s successes 24/7 through social media. So then we feel even more pressure to succeed. The thing is, success often takes years, if not decades to achieve. Sure, there are a lucky few who fell into the golden pot of success early on - shout out to Zuckerberg, J.Law and Lena Denham. But for the rest of us twenty-somethings, it ain’t always that easy. But fret not, many of the most successful people in the world were also fumbling through their 20s. So if you're late on the rent, stuck in a depressing job and have a dream but you see no way out, then check out this list of celebrities who also struggled in their 20s - it’ll make you feel better.


15 Tina Fey

Famous for her sexy-librarian schtick, Mean Girls (2004) and 30 Rock, Tina Fey came from humble beginnings. During her 20s, Fey worked on the front desk at the YMCA and   took evening acting classes to perfect her craft whilst living in a dodgy borough of Chicago. Fey did not get hired as a writer on Saturday Night Live until she was in her mid 20s, after some SNL writers discovered her at an improv group. Impressed with Fey's improv prowess and sketch ideas, they hired her as a staff writer. By 1999, Fey had climbed her way to head writer and remained there until 2006. Just think, if Fey had given up and resigned herself to a life at the YMCA, we wouldn't have the universally loved sport that is quoting Mean Girls (2004), and a world without Mean Girls (2004) is almost unimaginable.

14 JK Rowling


The woman who needs no introduction, J.K Rowling struggled for many years before Harry Potter became a success story, or stories - rather. Rowling first had the idea for Harry Potter when she was 25 whilst on a delayed train to King’s Cross in London. Soon after, she was fired from her job for daydreaming too much about Harry Potter. By 1993 though, Rowling had written the first three chapters of Harry Potter and the Philosopher’s Stone. Whilst living off welfare and being a young single mother, Rowling would write the rest of the Harry Potter novels in many cafes around Edinburgh. Edinburgh castle supposedly inspired Hogwarts. However, despite her brilliant imagination, Harry Potter and the Philosopher’s Stone was rejected several times by numerous publishers and did not get published until 1997 - seven years after she initially had the idea for the story. Success takes time, so be patient and keep cracking away. You know what they say, when the tough gets going just keep going.

13 Tim Allen

Best known for his role as Santa Claus and as the voice of Buzz Lightyear in Toy Story, Tim Allen had a rough start in his 20s. In 1978, when he was in his mid 20s, Allen was arrested for possession of over 650 grams of cocaine. To avoid a life imprisonment charge, Allen gave the names of other dealers and only received a sentence of three to seven years. He only ended up spending two years behind bars, though. After prison, Allen began working at an advertising agency and moonlighted at The Comedy Castle during the evenings. After being discovered by Disney and offered some roles, he turned them all down and fought to have his own routine, which soon turned into Home Improvement. Home Improvement launched Allen's career.

12 Johnny Depp


Before he brought to life Captain Jack Sparrow, Edward Scissor Hands and Willy Wonka, Johnny Depp struggled along in his 20s after dropping out of high school at the age of 15. After that, he fronted a band called The Kids but, struggling to survive financially, he worked as a telemarketer selling pens. At the age of 20, Depp was married to a 25 year-old make up artist. Following the marriage, Depp and his wife moved to L.A where Depp began to pursue acting. A year later, he met actor Nicolas Cage, who introduced Depp to a Hollywood agent. From there, he scored some small extra roles until he was cast in Nightmare On Elm Street in 1984. It just goes to show, you never know where you'll end up - one year you could be selling pens and the next you're acting in films. Life is full of surprises.

11 Brad Pitt


Here’s one for the college drop-outs: Brad Pitt studied journalism at the University of Missouri before dropping out in his last semester to chase his dream of being an actor. He was actually only a couple of credits short of a degree. After dropping out, he packed up his things and drove to Los Angeles where he worked a plethora of jobs for several months to support himself. These jobs included; driving strippers around in a limousine, dressing up as a chicken for a restaurant and delivering refrigerators. He was discovered by an agent whilst accompanying a fellow acting student to an audition. The other student was not chosen though - that's a little awkward, don't you think?

10 Ashton Kutcher


The star of That '70s Show and No Strings Attached (2011) worked at the same cereal factory as his father, sweeping cereal from the ground. He also donated his blood for money to support himself during college, where he was eventually discovered by an agent after competing in a modelling competition. Whilst he lost to (none other than) Josh Duhamel, he was offered a modelling contract with NEXT. From then on things sky-rocketed for the star after he moved to L.A and was cast as Kelso in That '70s Show. He has now starred in many other films including, Dude, Where's My Car (2000), Cheaper By The Dozen (2003), Killers (2010) and most recently, he replaced Charlie Sheen on the TV show, Two and a Half Men.

9 Sandra Bullock


After having dropped out of her acting degree to move to New York and study acting classes there, Sandra Bullock supported herself by working as a hostess, waitress and bartender at the same restaurant as actress, Jennifer Coolidge. Coolidge admitted that Bullock was so great at her job, she was given Coolidge's shifts. During this time, she took acting classes and scored a part in an off-Broadway play, where she was discovered by Alan J. Levi and was offered a part in the TV movie, Bionic Showdown: The Six Million Dollar Man and the Bionic Woman. She has since starred in Miss Congeniality (2000), Two Weeks Notice (2002), The Lake House (2006) and The Proposal (2009). It just goes to show that you can gain skills in any job - even if it feels like it's just a temporary gig.


8 Halle Berry


During high school, Halle Berry was an honor student, a cheerleader and an editor of the high school newspaper. Perhaps, the old chestnut of peaking in high school did not ring true for Berry. However, just like Brad Pitt, Berry dropped out of a broadcast journalism degree to pursue acting. She moved to New York but struggled with money and at the age of 21, she had to live in a homeless shelter for a short period of time. Later that year though in 1989, she was cast in the television show Living Dolls. However, during filming Berry fell into a coma and was later diagnosed with type 1 diabetes. Since then, she has starred in a plethora of films including, The Flintstones (1994), Die Another Day (2002) and Cloud Atlas (2012).

7 Hilary Swank

Best known for her roles in Boys Don’t Cry (1999) and Million Dollar Baby (2004), Hilary Swank came from humble beginnings, living in a trailer park. When she was a teenager, her parents divorced and her mother, realising her daughter’s desire to act, moved with her to Los Angeles where they both lived out of a car. Whilst she was working on Boys Don’t Cry (1999), the film that won her an Oscar, Swank was only earning $75 a day. By the end of the film, she had only made $3000 and had won an Oscar but was still not earning enough money for health insurance. Then, after winning her second Oscar, she was offered a part in a film that paid $500,000, whereas her Oscar-less male co-star was offered $10 million. Needless to say, Swank turned down that role.

6 Walt Disney


During his teen years, Walt Disney was rejected for military service and instead joined the Red Cross, driving an ambulance in France. It is said that his ambulance was covered in cartoon characters. By the time he was 22, he had been fired from his newspaper job for failing to be creative. Following that, he launched his company Laugh-O-Grams, which eventually became bankrupt. So, he decided to pack up everything and move to Hollywood. It was some time before he found success and he risked everything and failed a few times before he actually found success with Steamboat Willy (1928) and then Snow White and the Seven Dwarfs (1937). Walt Disney was nominated for 59 Academy Awards and still holds the record for the most Oscars won. This just goes to show that sometimes failure is just redirection towards something more fulfilling and promising.

5 Jennifer Lopez

via:ABC News

She’s been in over 30 films, made eight albums and is reportedly worth $250 million. But when she was 18, Jennifer Lopez was homeless and sleeping on a couch in her dance studio for months. However, this rough period didn’t last long as she landed a job dancing in Europe and upon returning to the United States, she was booked on the show In Living Color. Following that, she was cast in the film Selena (1997) and was nominated for a Golden Globe. After succeeding in dance and acting, Lopez then went on to release her first studio album On The 6. As they say, the rest for Jennifer Lopez is history. Man, talk about a triple threat!

4 Jon Hamm


After losing both his parents, the Mad Men actor first moved to LA in his early 20s with no more than $100 in his pocket. For many years, he worked as a waiter and a set designer for soft p*rn films. After not getting much work during his 20s, Hamm set his 30th birthday as a deadline to either start getting serious work or give up being an actor all together. Soon after he set this deadline, he began getting more work. First, he was cast in an episode of Ally McBeal as 'Gorgeous Guy in Bar'. In an interview with Entertainment, he said that he earned double the rate because the camera shot him for one second more. Since then, he has been cast in Mad Men, Unbreakable Kimmy Schmidt and Keeping Up With The Joneses (2016). Things have certainly been going great for Hamm.

3 Kristen Wiig

The Bridesmaids (2011) star worked a plethora of jobs before she was finally hired on Saturday Night Live. Kristen Wiig worked at a florist, at a hot dog stand and was hired to draw the post-surgery bodies of plastic surgery patients (just to name a few of the various jobs she took on). However, the very day she was supposed to start her new job, she decided to look at herself in the mirror and wondered what she would change about herself, and in that moment, she decided that acting would be it. The next day, she packed up her things and drove to LA. Talk about pursuing your dreams and acting in the moment.

2 Oprah Winfrey


The talk show goddess was actually once fired from her 6pm local news spot for getting too emotionally invested in the many stories she was presenting. Oprah Winfrey was down-graded to a daytime slot which turned out to be a blessing in disguise. The all happened at a time no one even knew who she was (or was going to become).

The Oprah Winfrey Show aired for 25 years and is today one of the longest-running talk shows ever. Oprah Winfrey is estimated to now be worth over $3.2 billion. Wow. Once again, sometimes failure is simply redirection to something greater, and Oprah really proves that.

1 Morgan Freeman

The actor best known for his oh-so velvety voice did not find success until he was already 52 years old, in the film Driving Miss Daisy (1989), which earned him a Best Actor nomination. He spent most of his 20s first in the US Air Force and then as a starving artist, working as a transcript clerk in LA whilst taking on some minor acting roles on the side. He first found success in the play Hello Dolly! in 1967. Well, since then Morgan Freeman has appeared in almost 100 films and he started getting cast halfway through his life - amazing. Today, everybody knows his name (and recognizes his voice, of course). This just goes to show that age is just a number.


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