1. Rosie Huntington-Whiteley

When she was just fifteen years old, English model Rosie Huntington Whiteley began working for the London-based agency, Profile. She left school and signed with the agency the following year, and first appeared in a Levi’s commercial. So what was Huntington-Whiteley’s first big purchase after she started earning big?

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She headed straight to the dealership and bought herself a new car of course. The only problem? She couldn’t drive it yet because she was too young to have her license. Huntington-Whiteley said that looking back, buying her first car — a Ford KA to be exact — wasn’t exactly the best purchase. At least now she can enjoy being chauffeured around with her husband, Jason Statham.

2. Shaquille O’Neal

Shaq has some pretty good advice for any up-and-comers who are about to cash their first big paycheck. He says to remember two things: FICA and sales tax. The basketball legend explained how he blew through $1 million in one day. First, he bought three black Mercedes, one for himself, his mother, and his father, for $500,000.

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Next, he wanted to accessorize for the upcoming NBA draft. That shopping spree included jewelry, a cell phone, suits, and a pull-out deck for his new car. But what was the best purchase that Shaq made early on in his career? A financial advisor. At the advice of some older NBA veterans, O’Neal hired a conservative advisor who has managed his money throughout his entire career. Shaq says that he has been like a father figure to him ever since.

3. Courteney Cox

Courteney Cox had already achieved some level of success in acting before getting her big break starring as Monica Geller on Friends. But this iconic part in what would end up being one of the most popular shows of the decade was a far cry from her first roles, in a Bruce Springsteen video and on daytime television.

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Cox said that the first thing she did when she landed her first paycheck from Friends was to go out and buy a car, an absolute must-have when living in Los Angeles. The ’90s star was one of the highest-paid TV actresses at the time, earning $1 million per episode during Friends’ last two seasons. More recently, she has said that she is re-watching the sitcom for the first time since going into quarantine in February 2020.

4. Matt LeBlanc

Matt LeBlanc’s date with success didn’t come quite as quickly as his Friends counterpart. Prior to landing his role as Joey, he had featured in a Heinz ketchup commercial, and had a recurring role on Married… With Children. When he auditioned for Friends, reportedly, LeBlanc only had $11 to his name.

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When the show first aired, the cast was making $22,500 per episode. By the series’ end, LeBlanc, like his co-stars, earned $1 million per episode for the last two seasons. Upon receiving his first paycheck, LeBlanc treated himself to a rather simple pleasure: a hot dinner, something he hadn’t been able to afford for a while as a struggling actor.

5. Chris Rock

Much like Shaquille O’Neal, Chris Rock forgot about a very important thing before going out and splurged with his first paycheck: sales tax. Recounting his first year on SNL, Rock said, “I made $90,000 and I bought a Corvette for $45,000. I’m thinking I’ve got forty five grand left!” At the end of his first year, Rock estimated that he was $25,000 to $35,000 in debt.

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Thanks to his awesome talent, Chris Rock would go on to become one of the most successful comedians in history. Eventually, he recovered the money and then some. Today, Chris Rock’s net worth is estimated at a staggering $100 million. It’s an incredible accomplishment for someone who grew up in public housing.

6. Kelly Rowland

When she was just seventeen years old, Kelly Rowland achieved instant fame alongside Beyoncé and Michelle Williams in Destiny’s Child. By the time she was twenty years old, she was a millionaire. When Rowland cashed her first paycheck, she had a unique idea. She decided to indulge in something that had always been forbidden to her.

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When she got her first paycheck, Rowland dashed to the grocery store and purchased all of the food that her mother used to say was too expensive. Rowland said it’s something that she will never forget because it was fun, and she funded everything herself. Her next big purchase, a 5,000 square-foot home was not the best investment, unfortunately. What does a 20-year-old do with all that space?!

7. Nicole Kidman

Nicole Kidman’s first purchase may seem trivial compared to her gargantuan level of fame, considering the Hollywood superstar is reportedly worth $183 million today. Prior to achieving international recognition opposite Val Kilmer in Batman Forever, she was a model and actress in her native Australia.

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Her first big purchase was a one-bedroom apartment in Mosman Village in Sydney for $81,000. Her second big purchase — a washer and dryer for her new home. These days, Kidman’s real estate portfolio has, shall we say, expanded, having since bought properties in excess of one million dollars in Los Angeles, New York, and London.

8. Rupert Grint

In perhaps one of the strangest celebrity first paycheck purchases on record, Rupert Grint, who played Ron Weasley in the Harry Potter series, bought an old Bedford van that was previously used as an ice cream truck. Describing the motivation behind his purchase, Grint said that being an ice cream man was something that he aspired to do as a child.

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But driving an ice cream truck comes with serious responsibility. Admittedly, Grint has driven the van around, and on multiple occasions has been stopped by children wanting to purchase ice cream…but he had none to give them. After a while Grint, finally stocked up and purchased a Mr. Whippy ice cream dispenser, and popsicles, which he occasionally gives out to kids in London free of charge.

9. Kerry Washington

Before achieving widespread fame from her roles in Mr. & Mrs. Smith and The Last King of Scotland, in the mid-2000s, Kerry Washington had played in a few minor roles on TV and in movies. Born in the Bronx, Washington once told an interviewer that Jennifer Lopez used to be her dance teacher growing up.

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The lessons paid off, because Washington’s first paycheck that stood out from the others before it came from 2001’s Save the Last Dance. She received her money in cash, which she hid underneath her mattress. Then, she went out and bought her first laptop computer with the money.

10. Serena Williams

Although tennis demigod Serena and her sister Venus come from humble beginnings growing up in Compton, California, Serena says that she never gave too much thought to her earnings. The 23-time Grand Slam winner says she has always played purely for the love of the sport. She credits her parents for teaching her about the value of money at a young age.

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Even though she lived in a two-bedroom house with seven people, Williams said that she never felt broke. Knowing her history, it probably comes as no surprise that upon receiving her first prize money, she took it directly to the bank. Unknowingly, she took her check through the drive-through, only to be redirected to go inside, after the teller learned the amount of the deposit.

11. Brad Pitt

Brad Pitt’s rags-to-riches Hollywood story is well-documented. The Missouri college student packed all of his belongings and dropped out of school just a few credits shy of his degree to give himself a shot at a big break in Hollywood. What’s less known is that Pitt has a passion for quality furniture, a love that he has nurtured since the early 1990s.

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After cashing in his first paycheck, Pitt has said that the first two items that he bought were a Craftsman chair and a Frank Lloyd Wright-wannabe lamp, all for his studio apartment. After that, he bought a stereo. Pitt’s furniture flair developed from a class he took at Missouri on Frank Lloyd Wright, which at the time was the only option to get out of a dreaded French class. The class, he said, changed his life.

12. Johnny Depp

Born in Owensboro, Kentucky, Johnny Depp was raised mostly by his mother, who worked as a waitress. Because of their stressful financial situation, the family was constantly shifting places, moving homes over forty times when Depp was a child, eventually settling in Florida.

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Though he describes their relationship when he was younger as having been tenuous, the first big purchase that Johnny Depp made wasn’t for himself. Instead, he used that first paycheck towards a 42-acre horse farm for his mother in Fayette County, Kentucky. The farm, which he put up for sale after the death of his mother, just sold in March 2020 for $1.3 million.

13. Lil Wayne

Dwayne Michael Carter, better known by his stage name Lil Wayne, wrote his first rap when he was just eight years old. By the time he was fourteen, he was already starting to earn real money from what would eventually be quite a lucrative career for him. The first time he realized he could “do a little something” with his money, he had received a check for $6,500.

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He tried giving the money to his mother, but she refused to accept it. Relishing in his newfound fame and money, Wayne purchased a Nissan Pathfinder. There was just one tricky issue: he wouldn’t be able to legally drive it for another two years. Wayne’s other investment, platinum and diamond-studded jewelry, was at least something he could show off (legally).

14. Rami Malek

Born in Torrance, and raised in the San Fernando Valley in Los Angeles, Rami Malek has said that he struggled as a child to assimilate with his peers. In his high school debate class, his teacher noticed his knack for interpretation, and encouraged him to join the school’s drama department.

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Malek would later study acting at Evansville University and in England, but at first he struggled to obtain work. He was working and living with a group of actors in New York, until his finances ran out, and he finally returned to Los Angeles. He nearly went into real estate before finally landing his first role on Gilmore Girls. After getting paid, Malek said that the first thing that he bought was an expensive espresso machine.

15. Madelaine Petsch

At only 25 years old, Madelaine Petsch doesn’t have to think too hard about what her first big splurge was…it wasn’t that long ago. The young actress is known for her role as Cheryl Blossom on CW’s hit show Riverdale, and she’s poised to become a household name in the near future.

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In order to introduce herself to fans off-screen, Petsch started her own YouTube channel, which has acquired several million subscribers and some lucrative business collaborations. She’s currently getting ready to launch her own line of active wear, so that she’ll have more money to splurge on. Her big purchase with her first big paychecks? A rose gold Cartier ring — in fact, she now buys a new one before the start of every season of Riverdale.

16. Donald Glover

Born and raised in Georgia, Donald Glover attended DeKalb School of the Arts. There, he was voted, “Most Likely to Write for The Simpsons” in his high school yearbook. A couple of years later while studying dramatic writing at New York University, Glover submitted a Simpsons script that he had written to television producer David Miner.

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Miner and Tina Fey were impressed enough with the sample to give Glover a writing gig for their NBC sitcom, 30 Rock — and the rest of his astronomical climb to superstardom is history. After securing his glorious first paycheck from NBC, he said that he went out and bought all the candy that he wasn’t allowed to eat when he was a kid, including his favorite, Gushers.

17.  Caleb McLaughlin

At just eighteen years old, Caleb McLaughlin has earned widespread fame for his recurring role as Lucas Sinclair in the Netflix hit series, Stranger Things. For his work, he has won awards from both the Screen Actors Guild and the NAACP. Surely the world has yet to see the best from McLaughlin.

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Off-screen, the young star is a known sneaker head and basketball fan, so it’s perhaps no surprise that his first purchase was a pair of Jordans. But precisely which coveted pair of kicks did he pick up? McLaughlin splurged on the Jordan retro XII wings model, which retails for about $225, if you can get them before they sell out.

18. Tiffany Haddish

Growing up poor in Los Angeles, Tiffany Haddish traveled a long road on her way to success. Raised mostly by her schizophrenic mother, she traveled by bus over an hour each way in order to attend a more prestigious high school. While working menial jobs in her twenties, she confessed that she spent many nights living in her car.

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After Haddish got her breakthrough in the mid-2000s, she said she used that first paycheck to buy a bunch of candy and corn nuts, snacks she was not allowed to get as a child. In other interviews, Haddish has also said that one of her first actions with her newfound wealth was to move her mother out of a mental institution. She then moved her grandmother, who suffers from Alzheimer’s disease, into the same house, with around the clock care.

19.  Jennifer Lopez

Growing up in the Bronx, Jennifer Lopez attended college for one semester to please her parents. She then dropped out to become a movie star, much to their dismay. She got her break when she won a contest to be a Fly Girl dancer on the NBC sitcom In Living Color.

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For years, Lopez, who was barely getting by as a dancer, drove a Honda hatchback that was given to her by In Living Color creator Keenan Ivory Wayans. After she’d saved up enough money, Lopez bought herself a Mercedes, and recalls crying in the dealership when she signed the lease.

20. Brie Larson

Brie Larson began acting at a young age as the youngest student ever admitted to the training program at the American Conservatory Theater in San Francisco. She soon became a regular on television, and played small roles in films before becoming a breakout star in the beloved indie film Short Term 12.

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The multitalented Larson, who once dabbled with a music career as a teenager, said that she purchased a blue electric guitar with the first paycheck she earned from her acting. More recently, she has put her skills on display, as well as the guitar itself, covering Taylor Swift’s “The 1”.

21. Marc Wahlberg

Marc Wahlberg has often spoken about his tough childhood, growing up the youngest of nine children in Dorchester just outside of Boston. Although Marky Mark and the Funky Bunch would become household names by the time Wahlberg turned 19, before then, he was just scraping by.

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Having dropped out of school, Wahlberg worked a variety of jobs, including as an auto mechanic and car flipper. After he and his group scored a number one hit with “Good Vibrations”, Wahlberg went out and bought himself a Mercedes. However, he couldn’t afford the insurance for it. Worse yet, it became a target for neighborhood toughs, who used to cut open the roof and steal his radio.

22. Mark Cuban

Mark Cuban’s story is one to be admired. The average Joe-turned-billionaire has worked for most of his life and has built a fortune without depending on others. Even before he was a teenager, he was always looking for a way to make money. Some of his earliest jobs include slicing cold cuts in a deli, selling newspapers, and selling powdered milk.

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Around this time, a young Cuban asked his father for a pair of basketball shoes. When his father responded that if he wanted the shoes, he should go out and get a job to pay for them himself, he did exactly that. He sold garbage bags to get the coveted pair of kicks that he wanted. Of course, now, he owns an entire basketball team.

23. Colin Kaepernick

After being taken in the second round of the 2011 NFL draft by the San Francisco 49ers, Colin Kaepernick signed a five year rookie deal worth over $5 million. He was used sparingly during his rookie and sophomore season, but came to prominence in 2014 signing a contract extension with the 49ers worth $126 million.

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Immediately after signing, Kaepernick pledged that he would give $1 million to various community organizations that he felt could take a stand against police brutality. He is known more today for his actions off the football field. Despite his obvious talent, he has by and large been blacklisted from the NFL on account of his political and social activism.

24. Judith Sheindlin

Before her rise to fame on daytime TV as Judge Judy, Judy Sheindlin and her husband Jerry were civil court judges living in a one-bedroom apartment in New York City. They drove a secondhand car, and generally lived pretty frugally. “My underwear was from Costco,” Sheindlin said in a candid interview with Page Six.

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Once Judge Judy landed her gig on television, the couple’s financial situation turned around. She was making three times as much on TV as she did when she was an everyday judge. The first thing she splurged on? Shoes! Used to buying everything on sale, she went the distance and paid full price for a pair of black Robert Clergerie shoes. Sheindlin’s net worth is now a reported $250 million.

25. Dave Grohl

Dave Grohl hit it big when he was still quite young. At just 22 years old, Grohl started making serious money in the early ’90s, catapulted into the limelight by the fame of his band Nirvana, an exposure that only increased after the death of frontman Kurt Cobain.

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In an interview with Variety, Grohl said that the first thing that he bought with his money was a beach house in North Carolina, along with a smoker and a bunch of barbecue. He said he basically lived off of pulled pork from age 22 to 25. Now that Grohl’s net worth is somewhere in the range of $280 million, let’s hope that he has diversified his dietary habits.

Sources: Business Insider, Rolling Stone, People