The Surprising First Paychecks of 20 Rich and Famous People

Mandatory Credit: Photo by Stephen Lovekin/Shutterstock for AWNewYork (14150804hi)15 Seasons of Shark Tank - Mark Cuban - Founder of Mark Cuban Cost Plus Drug Company, owner of the 2011 NBA Champion Dallas Mavericks, Mark Cuban CompaniesAdvertising Week New York, Day 2, The Penn District, USA - 17 Oct 2023.
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Everyone remembers their first real job and more importantly, that first paycheck. Usually, it’s something fairly menial and not exactly well-paying, like say, washing cars or flipping burgers. Still, there’s nothing quite like your first whiff of financial independence.

Guessing someone’s first job can be almost impossible to do because it often has absolutely nothing to do with how they make money now. When it comes to their career, successful millionaires and billionaires had to start somewhere.

The same can be said for many of the rich and famous. Despite their current celebrity status and influence, there are plenty of superstars whose foray into the working world was humbling, to say the least.

For example, Taylor Swift tended to the Christmas tree farm she was raised on from ages 5 to 10. Her “job” was to pick the praying mantis pods off of the trees so that they wouldn’t hatch inside people’s homes. 

Plenty of superstars have similar backstories. Here are 20 rich and famous stars’ surprising first jobs and what they earned.

Mark Cuban: Garbage Bag Salesman

Mark Cuban is world-famous for his business acumen, but his beginnings were humble to say the least. His first gig was selling garbage bags.

“I sold garbage bags door-to-door when I was 12 years old because my dad told me the only way I could get new basketball shoes was if I had a job,” the “Shark Tank” star said on a 2019 episode of GQ’s “Actually Me.”

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Cuban sold the boxes of garbage bags for $6, which was a markup from the $3 he purchased them for, and used his own script to do so.

Jennifer Aniston: Bike Messenger

It’s hard to imagine the always well-manicured Jennifer Aniston pedaling around New York City for work, but that’s what she did for a living in her pre-A-list celebrity days.

“(The) toughest job I ever had was being a bike messenger in New York City,” Aniston said during a 2011 press conference, Movieline reported. “I was 19.”

And according to the Bureau of Labor Statistics, the current hourly rate for couriers is about $25 an hour. Back when Aniston was 19, the rate was probably lower.

Steve Buscemi: Firefighter

“Boardwalk Empire” star Steve Buscemi worked as a New York City firefighter for four years beginning when he was 22 years old, The Hollywood Reporter reported. He even returned to the firehouse as a volunteer after the Sept. 11 attacks.

The current median salary estimate for a firefighter is about $57,120 annually. 

Jim Carrey: Janitor

When he was 14 years old, Jim Carrey and his brothers got jobs at the tire factory where their father worked. They worked eight-hour shifts after school as janitors and security guards, according to the Hollywood Reporter.

The median hourly wage for custodial workers is just under $17.

Bradley Cooper: Doorman

While he was getting his MFA at NYU, Bradley Cooper worked as a doorman at the Morgan Hotel in New York City. As of last year, the average hourly pay for a Union Doorman in New York is $20.64 an hour.

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“There were three candles in the lobby and they said, ‘Always keep them lit,'” he said. “But the door would open and they would go out, so I spent most of my time trying to relight those candles.”

Miley Cyrus: Stage Cleaner

Miley Cyrus often went on tour with her dad, Billy Ray Cyrus, which is admittedly pretty glamorous, but it seems to have had its grueling moments.

It was Miley’s job to go on stage after the show to collect all the bras and underwear that had been thrown onto it, she told Rolling Stone. Billy Ray paid her $10 for the gig.

Harrison Ford: Carpenter

Harrison Ford said in a Reddit Ask Me Anything that when he was cast as Han Solo in the original “Star Wars” film, his main job at the time was working as a carpenter. With the first “Star Wars” releasing in 1977, his pay was likely a far cry from a current carpenter’s median pay which is about $56,350 per year.

Whoopi Goldberg: Mortuary Makeup Artist

Whoopi Goldberg had plenty of experience with dead people before starring in the movie “Ghost.”

“I did hair and makeup on dead people,” she said on “Oprah’s Master Class.” “There was an ad in the paper. And I’m a licensed beautician as well, because I went to beauty school.”

According to data from ZipRecruiter, a mortuary makeup artist makes approximately $25 an hour.

Hugh Jackman: Gym Teacher

Before his movie stardom, Hugh Jackman worked as a boys’ gym teacher at England’s Uppingham School, CBS News reported. For perspective, an average high school teacher currently makes a median salary of about $65,220 annually. 

Dwayne ‘The Rock’ Johnson: Dishwasher

Dwayne Johnson is one of the highest paid actors in the world, making an estimated $20 million per film, but his first job’s pay was a far cry from the millions he brings in today. Johnson tweeted that he got his first job at 13 years old, working night shifts as a dishwasher.

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“These days I still wash every dish,” he said.

Nicole Kidman: Massage Therapist

Your masseuse could end up being the next Nicole Kidman. The actress confirmed to The Daily Beast that she once worked as a massage therapist to help support her family.

“My mother had breast cancer, and so when you go through radiation, you get terrible seizure of the muscles, so I took the massage course and then I liked doing it, so I started to go around to people’s houses and do massages,” she told the site.

Madonna: Dunkin’ Sales Associate

Madonna worked several part-time jobs in New York City before she became the Queen of Pop, including a short stint at a Dunkin Donuts on 57th Street. She was fired after squirting filling all over a customer, according to a biography of the singer written by Mary Cross.

Meghan Markle: Calligrapher

It’s common knowledge that Meghan Markle worked as an actress before marrying into the British royal family, but she held another job before getting her big break on “Suits”: calligrapher.

According to People, Markle worked at a Paper Source in Beverly Hills, California, as a calligraphy instructor, and also worked as a freelance calligrapher on the side. 

Rachel McAdams: McDonald’s Drive-Thru Worker

Rachel McAdams worked at McDonald’s for three years when she was a teenager, but told Glamour that she wasn’t a very good employee.

“It was a great place to work, but I had a little bit of an OCD thing with hand washing and just didn’t have time,” she said. “They were like, ‘Hey, the drive-thru’s backing up. Stop washing your hands!’ I was not a great employee; I broke the orange juice machine one day.”

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Melissa McCarthy: Starbucks Barista

Melissa McCarthy worked as a Starbucks barista when she first moved to Los Angeles to pursue acting. She told Conan O’Brien on his late-night talk show that she once even served Chris Farley, who was a comedy idol for her.

“At one point, I got so overwhelmed because he was right there, that I started crying,” she said.

Nicki Minaj: Customer Service Representative

It’s hard to imagine fiery rapper Nicki Minaj working as a customer service representative, but it was one of the odd jobs she held after graduating high school.

“I like dealing with people, but I don’t really like a lot of [nonsense], so maybe customer service wasn’t the best job for me,” she told GQ.

She also worked as a Red Lobster server but was fired from that job after chasing a couple into the parking lot for stealing her pen.

Barack Obama: Baskin-Robbins Employee

Former President Barack Obama worked at Baskin-Robbins as a teenager when he was growing up in Honolulu, he shared on a LinkedIn blog.

“My first summer job wasn’t exactly glamorous, but it taught me some valuable lessons,” he wrote. “Responsibility. Hard work. Balancing a job with friends, family and school.”

Amy Poehler: Ice Cream Scooper

It’s not just the former president who started out at an ice cream shop. Comedian Amy Poehler worked at a local ice cream parlor during the summer before she went to college.

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She penned an essay about her experience for The New Yorker, noting that it wasn’t your typical “romantic” summer job: “Hard and physical, the job consisted of stacking and wiping and scooping and lifting.”

Harry Styles: Bakery Worker

When he was 14, Harry Styles worked at a local bakery for 6 pounds ($7.80) an hour, The Daily Mail reported. He quit the job to audition for “X Factor.”

Kanye West: Retail Employee at the Gap

Kanye West has worked in fashion since a very early age. When he was a high school student, he worked part time at the Gap.

“When I was working at the Gap at 15, I don’t think I had any desire to actually make clothes, but I always felt like that’s what I wanted to be around,” he told Paper magazine. “I loved the fabrics, I loved the colors, I loved the proportions.”

Gabrielle Olya contributed to the reporting for this article.

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