15 Successful Celebs Who Struggled In Their Twenties

Your twenties are a hard time. You don’t know which decision you make that will be a straight path to the life you always wanted, or the path right to the unemployment line. There is a constant level of fear over everything you do, and a level of uneasiness. This is the first time you won’t have school, the first time you will have a real job and the first time for a lot of things. It’s so easy to think that you don’t have it all together in your twenties.

But the good news is that you don’t need to have it all together because having it all together is a myth. It’s a lie because even those people who seem like they have it together on social media, are scrambling to try and make it look that way. Everyone is just trying their best to fake it until they make it.

Don’t believe me? Here is a list of 15 celebrities that really didn’t have it together when they were in their twenties. These are some really powerful and successful human beings of their time, and if they didn’t have it all figured out then, why do you need to?

15 Sylvester Stallone


Even if you haven’t seen one of Stallone’s movies, you know who he is and how someone would impersonate him. In the 70s into the 80s there wasn’t an action movie that didn’t have him in it. And he is still a prominent figure today. It’s hard to imagine that Rambo ever struggled to get to where he is.

When he started his career, it was rocky to say the least. He had a couple of unaccredited minor roles in some movies. But the really scandalous part is how he starred in a soft-core adult film. He addressed it later on, saying that he was desperate for money after being evicted from his apartment, and he spent three weeks living in the Port Authority bus terminal.

14 Steve Carell

Via: boomsbeat

Today, Steve Carell is one of the most recognizable actors in both television and movies. He spent years playing the beloved Michael Scott on The Office and has had a string of highly successful films, which range from dramatic to hilarious.

But before all of that, he was just a regular guy from Massachusetts. One of his first jobs out of college was a mail carrier, but after six months he quit because his boss told him he wasn’t good at his job and needed to go faster.

13 Hilary Swank


Who knew the Million Dollar Baby herself struggled to get to where she is today. Before she won countless awards for some of the greatest movies in the past twenty years, she was a struggling actress who went through a lot to get to where she is today.

12 Lucille Ball

Via: pinterest

For a lot of us, when we hear the name Lucille Ball, we think of I Love Lucy, and one of the most iconic women in comedy. To think of a time when she wasn’t the powerhouse that we know her as is almost unbelievable to us.

Before she was even in her twenties, she was diagnosed with rheumatoid arthritis and had to stop working for two whole years. When she came back into show business, she went to Broadway, but was hired and fired pretty quickly. When she was 22, she moved to LA to act, where she had small roles in a lot of movies, but nothing landed. She was dubbed the “Queen of the B’s,” meaning she was in a lot of B-movies.

11 Jon Hamm

Via: slate

Jon Hamm was relatively unknown before Mad Men, which has skyrocketed his career and earned him many award nominations. But before he was Don Draper, he was just a kid out of college, who worked at his old high school as an acting teacher.

When he was 24, he moved to LA to pursue acting, during which he waited tables and lived with four other aspiring actors. While many people his age were getting roles to play younger characters, Hamm simply wasn’t making the cut. After three years of rejections, his agency dropped him. Talk about a low point.

10 Ralph Lauren


Born Ralph Lifshitz, the man better known as Ralph Lauren wasn’t always the billionaire fashion designer we know today. Before he was one of the most well-known fashion designers in the world, before he had his own stores everywhere, before the USA Olympic team wore his apparel - he was struggling through his twenties.

9 Harrison Ford

Via: Nerdlowdown

Long before he was Han Solo or Indiana Jones - basically before he was one of the most popular actors in Hollywood, Harrison Ford was a kid just trying to make it.

His first time acting was his last semester of college in a drama class. After graduation, Ford moved to LA to apply for radio voice-overs - which he didn’t get. He eventually signed a deal with Colombia pictures for their New Talent Program, for $150 a week, playing small roles in films. He was in countless films - in the background, or not talking, but most importantly, not getting credited.

8 Tim Allen

Via: majorten

We’ve been in love with Tim Allen for years. From his time as Tim "The Tool Man" Taylor, to his voice acting as Buzz Lightyear, to Santa Claus himself. Tim Allen is a household name, one which we are comfortable with our kids watching on TV, one we feel is like a neighbor to us. But he wasn’t always this safe, respectable actor.

He started his career in comedy on a dare when he was only 22 in a suburb of Detroit. He worked his way to the city, working comedy clubs, and eventually made his way to LA. He was a regular at The Comedy Store and even landed on some late night talk shows. It all seemed like it was going well for the young comedian.

7 Zack Galifianakis

Via: youtube

Zach’s rise to fame didn’t come until his breakout role as Alan in The Hangover in 2009 when he was 40. Since 2009 his career has skyrocketed, with significant roles in some of the best comedies to date, but before that he had a rough go of it.

To start his twenties, he dropped out of North Carolina State University, after being one credit short of graduating. After that, he left the south and headed up to New York City. There he worked as a bus boy for a high-end strip club and a series of other odd jobs while polishing his stand up routine.

6 Kristen Wiig

It’s only recently that Kristen Wiig came into the spotlight and became a household name. Even though she had been on SNL from 2005-2013, it wasn’t until the huge success of Bridesmaids in 2011 that she became a household name.

She came to acting during college, and her professor told her to continue with the craft. During the summer before he second year, she worked at a plastic surgeon’s office, drawing post surgery pictures for the patients. Instead of going back to school, she dropped out and moved to LA to give acting a real shot.

5 Morgan Freeman

Via: smashinglife

It’s hard to imagine Morgan Freeman not as successful as he is today. The man literally played God in two movies. He has been in so many incredible films in the past thirty years. But there was, in fact, a time where he was struggling with paying the rent.

After graduating high school, he turned down a drama scholarship from Jackson State University to go into the Air Force. After four years in the military, he moved to LA to pursue acting. He was trying to join the actors’ union, but he didn’t have a job - which he called a catch 22. He was literally a starving artist for his first couple of months that he lived in LA. He had unaccredited roles; he had bit parts, he even danced.

4 Tina Fey

Via: focusfeatures

Tina Fey has done a lot in the past ten years. She wrote and created the Emmy award winning 30 Rock, and brought to life the fantastic Liz Lemon. She brought us one of the best movies of our time, Mean Girls. In fact, it’s hard to find a movie that Fey has been in that wasn’t laugh out loud funny.

She’s done so much since her days on SNL; it’s hard to remember that her beginnings are so humble. Before she was the Weekend Update anchor with Jimmy Fallon, she was a writer. And before all of that, she was in Chicago.

3 JK Rowling

Via: bustle

Yes, Rowling had the initial idea for Harry Potter when she was 25, but the idea for a first book and success are not synonymous. She was working for Amnesty International as a bilingual secretary at the time, and she was day dreaming about wizards a little too much for her bosses. She was fired.

To make matters worse, her mother died when Rowling was 25 as well. She didn’t even get to tell her mother about her idea for Harry Potter.

2 Walt Disney

Via: thedailybeast

It’s hard to imagine the man behind one of the largest companies in the world ever struggled. Before there were theme parks, before there were feature length films, and even before Mickey - Disney struggled.

With a failing cartoon advertising business in Kansas City, Disney became bankrupt. Disney moved to Hollywood, even though the cartoon industry was largely in New York, with not much to his name. He had small success with Alice’s Wonderland, a short silent film which lasted for a couple of years. The real drama came when he created Oswald the rabbit, which Disney wasn’t properly paid for, and he lost both the rights to his creation and his team.

1 Oprah

Via: icon360.blogspop

Oprah is not only one of the wealthiest people in the world, but she is also one of the most influential. Millions of people hang on every word she says, buy her magazine, watch her television channel and follow her on social media. Sometimes we forget that she comes from such humble beginnings.

She was born into rural poverty in Mississippi to a teenage mother. Her upbringing was far from easy. She moved around a lot, was sent to live with her father and had been molested by family members - but in spite of all of that, she went on to receive a full scholarship from Tennessee State University.

Her first job after college was in Baltimore as an anchor for the 6 p.m. news, but that didn’t last long, she was taken off the air to work a lower level job. After a while, she was recruited to co-host a local talk show, “People Are Talking.”

It wasn’t until her late twenties when she first moved to Chicago to host AM Chicago, which would later become syndicated and renamed to The Oprah Winfrey Show.


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15 Successful Celebs Who Struggled In Their Twenties