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10 Celebrities Who Didn't Have It Easy In Their 20s

Most people's 20s are a time of transition, understanding and in some cases, hardship, and the younger years of many celebrities' were no exception.

With that in mind, and with people in their 20s often feeling burdened by a weight of expectation, The Celebrity Lane has profiled 10 celebrities whose life changed forever during their 20s.

1. Ashton Kutcher

Ashton Kutcher didn't have it easy growing up, and though his playful persona on his MTV show 'Punk'd' may suggest otherwise, his past is probably one he looks back on with sadness. Not only did he contemplate suicide to provide a kidney for his dying brother, but he was also kicked out of high school and ostracised by his local community after being caught stealing money from them.

Despite these hardships, Kutcher managed to gain a place at the University of Iowa, and upon returning home for the holidays, a 20-year-old Kutcher would sweep cereal off the ground of his father's factory before being scouted by a model agent who persuaded him to enter the "Fresh Faces of Iowa" competition. 

After the contest, which would see him finish runner-up to none other than Josh Duhamel, Kutcher signed with NEXT Model Managment before transitioning to acting.

2. The Weeknd

Abel Tesfaye, now known by his stage name, The Weeknd, was an enigma the moment he uploaded his first three tracks on YouTube shortly after turning 21. But the Toronto native's road to success, just like his louche music, is unique, and his transformation into the artist we know today makes for a spectacular story. A story that began at 17 when he and best friend Lemar left their respective homes and school with just a mattress and a hired removal van to their name.

In the years that followed, Abel and Lemar would claim benefits and sell soft drugs on the side, all while partying to the extreme, a period that perhaps unwittingly served as a muse to the nihilistic lyrics that characterised his first three mixtapes. But it wasn't just the music. What ironically gained him notoriety was his refusal to give interviews and never include his face in his videos, and shortly after the word-of-mouth success, the singer made his first live performance at Tronto's Mod Club.

More gigs followed, and after the release of three mixtapes, now known as The Trilogy, the once homeless teen and 21-year-old American Apparel assistant was signed to Universal Republic the following year. 

3. Brad Pitt

If ever there was celebrity story that chronicles the struggles of a twenty-something artist, then Brad Pitt's may just top them all. Unlike Ashton Kutcher and The Weeknd, Pitt's success didn't come early in his 20s, and it wasn't until he was 24, following gruelling hours working as a chauffeur, dressing up like a chicken at a restaurant and delivering refrigerators, that he gained his first acting credits.

Even then, Pitt's career didn't exactly take off, and it was only after turning 27 that he earned his first leading film role.

4. Halle Berry

Like Brad Pitt, Hale Berry was studying broadcast journalism, and would often take on shifts in the children's department at Higbee's to fund her course. However, with a face like Berry's, many beauty contests came calling, and she was winning many of them, which soon gave her the confidence to follow her dreams and pursue an acting career in New York.

But it wasn't plain sailing, and up until the age of 23, the acting-student resided in a homeless shelter having run out of money. However, her 23rd year would also see her catch her first big break following a successful audition for a part in the ABC series, Living Dolls. 

Now 52, the Oscar-winning actress has overcome her fair share of obstacles to get to where she is.

5. Chris Rock

Chris Rock is one of America's best-loved comedians, and his tours generate millions of dollars, but it wasn't all fun and games for Rock, who worked menial jobs at various fast food restaurants across New York until his early 20s before his standup career took off.

Speaking about the time he worked at Red Lobster, Rock thought it ironic that his minimum wage couldn't even afford the cheapest item. “The thing about Red Lobster," he said, "is that if you work there, you can't afford to eat there. You're making minimum wage. A shrimp costs minimum wage."

6. Hillary Swank

The Academy Award winner is known for portraying characters from rough backgrounds in films such as Million Dollar Baby and Boys Don't Cry, and part of the reason she did so well can be attributed to her background, which saw the actress raised in a trailer park in Washington Sate.

But things only got harder, and upon her parent's divorce at 16, her mother selflessly decided to move to Los Angeles to support Swank's acting career, all while living in a car for long periods. 

Even after gaining her first significant roles at the age of 20, Swank and her mother were hardly wealthy and by the time she hit the big time in her Oscar-winning role of Brandon Teena in the powerful 1999 film Boys Don't Cry, the then 23-year-old was only earning a meagre $75 a day.

7. Oprah Winfrey

If ever there was an article profiling the greatest rags-to-riches stories, then you'd be hard-pressed not to include Oprah Winfrey. Sexually abused for most of her childhood when her mother was away working, it was only after her father, Vernon Winfrey, took her into his Nashville home that thing's started looking up. By her admissions, her father was a strict disciplinarian, but from his guidance, his daughter developed a love for learning, which would lead to Tennesse University offering her a scholarship.

Upon graduating, Oprah had her heart set on journalism, and quickly established herself in the local news scene, although she was demoted from an anchor role when she was 23 for being too emotionally invested in the stories, and it wasn't until AM Chicago gave Oprah a talk show at the age of 28 that things took a life-changing turn for the local television personality.

8. Sandra Bullock 

The Oscar-winning actress regularly tops the best-paid lists in Hollywood, but Bullock's life hasn't always been one shrouded in glitz and glamour. Coming from a regular middle-class family, the 51-year-old spent the majority of her childhood in Germany and only returned to America to study Drama at East Carolina University before moving to New York City after graduating to persue professional roles.

It was then that the jobbing 22-year-old actress worked for many years as a bartender and cocktail waitress, which would see her come into contact with fellow actress Jennifer Coolidge, who has previously admitted that most of her shifts were given to her colleague because she was a better waitress.

9. Jon Hamm

Jon Hamm only had $100 to his name when he first moved to Los Angeles in his early 20s following the death of both parents, and it wasn't until his 30th birthday that things started looking up for the actor.

And while John Hamm now personifies cool after gaining fame in AMC's hit series 'Madmen', the years leading up to the role were anything but, with Hamm making ends meet as a set designer for porn movies in the valley. The television star also taught high school drama back in his home state of Missouri. 

10.  Kristen Wiig

Making her name on Saturday Night Live,  Kristen Wiig had many jobs before she landed the coveted gig, which included work as a florist, a hot dog vendor and drawing the post-surgery bodies of plastic surgery patients.


Wiig continued working odd jobs in Los Angeles right up until she was 30, upon which she was cast on the Spike TV show The Joe Schmo Show, leading to her big break on SNL two years later.

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