NASCAR as a sport has seen celebrities and pop stars throughout its history. From performing, and calling drivers to start their engines to being a part of a team, stars have always taken an interest in the sport. While there are friendships building between NASCAR drivers and celebrities, like Denny Hamlin being friends with Michael Jordan, or Justin Marks with Pitbull, things just step up if they are childhood friends. Recently, the Wood Borthers Racing superstar has responded to something of this sort about his personal life.
With his first Cup Series victory at Las Vegas Motor Speedway victory, Josh Berry not only cemented his place in NASCAR’s top tier but also delivered Wood Brothers Racing its first triumph in years. Piloting the No. 21 Ford Mustang for Wood Brothers Racing, Berry steadily worked his way through the field, running inside the top 10 for most of the race. However, even as his on-track success continues to grow, it’s his personal life and past connections that have unexpectedly drawn as much attention as his racing achievements.
Clarifying his connection to Taylor Swift
During a recent interview, Josh Berry addressed an intriguing detail from his past: he attended the same high school as global pop sensation Taylor Swift. However, he was quick to clarify that their connection is often overstated.
“She wasn’t a classmate. I think she was a grade above me,” Berry explained, dispelling misconceptions about their time at Wyomissing Area Junior/Senior High School in Pennsylvania. The topic arose when the interviewer asked, “What’s been mentioned more, your past life as a bank teller or having gone to the same high school as Taylor Swift?“
Without hesitation, Berry responded, “Both, definitely the Taylor Swift one.” His answer underscored how, despite his racing achievements, a seemingly small detail from his past had generated outsized interest.
He elaborated on how the topic gained unexpected traction. “It’s one of those things you mention one time, and you don’t realize how big of a deal it’s really going to be. It’s kind of like, hey, tell us something interesting about yourself. And you mention it, and it turns into a way bigger deal than you expect.”
Josh Berry on life a few days after his inaugural Cup victory, the questions about going to the same high school as Taylor Swift, if he has heard from anyone at the bank he has worked at and getting ready for Homestead. @NASCARONFOX pic.twitter.com/P3IyV0juoE
— Bob Pockrass (@bobpockrass) March 20, 2025
This comment reveals the reality of fame in the modern era, where even the most casual personal anecdotes can spiral into widespread intrigue. Despite never having a personal relationship with Swift, Berry has repeatedly been asked about their high school connection, proving just how fascinated people are with any link to the world’s biggest pop star.
When the interviewer pointed out, “Not a lot of people could say they went to high school with the most iconic performer in the world right now,” Berry acknowledged the significance but reaffirmed the distance between them. “No, no, you’re right,” he said, subtly recognizing Swift’s cultural dominance while maintaining that their connection is circumstantial at best.
Berry also recalled hearing about Swift’s early performances at school talent shows, though he admitted he wasn’t personally involved. While some of his friends had interacted with her, his own high school experience was largely separate from hers.
The renewed fascination with this anecdote coincides with heightened media attention on Swift due to her relationship with NFL star Travis Kelce, further amplifying interest in Berry’s distant connection to the pop star.
Though the Taylor Swift story has captured headlines, Berry remains laser-focused on his racing career, one that has taken an unconventional path compared to most NASCAR drivers. Unlike many competitors who come from wealthy racing families, Berry did not grow up with significant financial backing. Instead, he balanced his racing aspirations with a full-time job as a bank teller at a Wells Fargo branch in Tennessee.
This past life often comes up alongside his Swift connection, with the interviewer asking if any former coworkers had reached out after his recent success. Berry responded, “Not that I know of. I mean, I got probably around 400 text messages. There’s several in there that are numbers that I don’t have. Some of them were 615 numbers, which is Nashville area. So it’s hard to say if I have or not. But I know that several of them still pay attention to our racing and are fans of it.”
This response not only highlights the overwhelming amount of support he has received but also reveals the grassroots loyalty that NASCAR fans have. Unlike other sports, where athletes are often distanced from their early lives, many of Berry’s former colleagues and acquaintances still follow his career, illustrating his relatability and connection to everyday working-class people.
The unconventional path to success
Berry’s unconventional path to NASCAR is another factor that makes his story stand out. Unlike drivers who rise through the ranks with the backing of major sponsors or family funding, Berry caught his break in an unexpected way, through iRacing, a virtual racing platform. His digital performance caught the attention of Dale Earnhardt Jr., who recognized his raw talent and brought him into JR Motorsports in 2010.
This method of discovery was unheard of at the time, and his ability to transition from simulation racing to dominating in Late-model racing set him apart as a unique talent. His rise was further solidified when he won the prestigious 2020 NASCAR Advance Auto Parts Weekly Series national title, proving he wasn’t just an online sensation, he was a real-world contender.
Born in Hendersonville, Tennessee, Berry started racing go-karts at age eight before advancing to Legend Cars and Late Model Stock Cars. After years of grinding through the ranks, his persistence paid off when he transitioned to the NASCAR Xfinity Series in 2021, where he won multiple races.
In 2024, he secured a full-time Cup Series ride with Stewart-Haas Racing, and now, driving the iconic No. 21 car for Wood Brothers Racing, Berry recently achieved his first Cup Series win, cementing his status as one of NASCAR’s emerging talents.
Beyond his racing career, Berry is also known for his deep appreciation of NASCAR’s history. Unlike many modern drivers, he studies legendary figures like David Pearson, Cale Yarborough, and Dale Earnhardt Sr. to refine his driving style. Additionally, he maintains close ties to grassroots racing, frequently returning to short tracks to mentor young drivers. His willingness to stay connected to the racing community further distinguishes him in an era where many drivers are increasingly focused on corporate branding.
Despite the media frenzy surrounding his ties to Swift and his unique journey, Berry remains committed to his craft. When asked about his future goals, he emphasized his focus on performance: “I feel completely prepared…I hope we can build off last year’s strong run.”
This statement underscores his determined mindset. While many might let outside distractions affect their careers, Berry remains laser-focused on racing. His ability to compartmentalize media attention while staying locked in on his on-track goals is a testament to his professionalism.
While his past anecdotes may intrigue fans, Berry’s perseverance, unconventional path, and sheer dedication to the sport remain the real story. As he continues to develop in the Cup Series, his ability to thrive under pressure will determine just how high he can climb in NASCAR history.
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