Josh Berry has experienced firsthand the difficult path to NASCAR’s premier Cup Series, where the competition is more exacting than many realize. Now a Cup driver with Wood Brothers Racing, Berry’s journey from iRacing and local short tracks to his first Cup victory this season highlights the challenges and persistence required to succeed at this level, shedding light on the true nature of the Josh Berry NASCAR Cup challenge.
The True Difficulty of Racing at NASCAR’s Highest Level
Berry recently opened up about the stark contrast between his initial expectations and the reality of racing in the Cup Series during an interview with Jeff Gluck from The Athletic. He explained that while success seemed attainable when winning in Late Models, the level of talent and competition in the Cup Series is extraordinary and unpredictable factors heavily influence race outcomes.
“It’s way harder than people realize. When I was racing Late Models and winning all kinds of races, you’d see guys come through the ranks… They’d win a Truck race or whatever. And all of us at that level thought, ‘We could do that if we had the opportunity.’ But living it, you realize just how good everyone is in the Cup Series and how hard it is to be competitive – and how much is outside of your control,” Berry said.
—Josh Berry, NASCAR Cup Driver
This perspective is shaped by Berry’s unique path through the racing ranks. Discovered by Dale Earnhardt Jr. through iRacing, Berry was given a chance with JR Motorsports’ late model program. He capitalized on that opportunity by winning the CARS Tour championship in 2017 and the NASCAR AAA Weekly Series title in 2020.
Progressing Through the NASCAR Ladder
Berry’s success in late models paved the way to the Xfinity Series, where he earned his first win at Martinsville in 2021 and eventually reached the Championship 4 before moving up to the Cup Series. However, Berry notes that the biggest adjustment has been the limited control he has once he reaches the top level, a sharp contrast to the hands-on involvement he had earlier in his career.
“When I was Late Model racing, I worked on my car every day. We had a close-knit group making decisions on setup and tracks. Now you get to the Cup Series and there’s so much outside of your control. You can have the best car and still have a bad pit stop or bad restart. I knew it would be hard, but it’s amazing how good these teams and drivers are,” he added.
—Josh Berry, NASCAR Cup Driver
The increase in variables beyond his influence highlights the complexity of competing in the Cup Series and emphasizes how crucial it is to rely on a strong team and flawless execution in every aspect of the race weekend.
Milestones and Momentum Heading into the Playoffs
Berry’s breakthrough moment came in March at Las Vegas, where he claimed his first Cup Series victory. This win not only locked him into the 2025 playoffs but also marked Wood Brothers Racing’s 101st win in Cup history. Despite some inconsistent results during the summer, including five finishes outside the top 20 over ten races, Berry’s recent back-to-back top-10 finishes at Richmond and Daytona signal a return to form for the No. 21 team.
The Cup playoffs begin on August 31 at Darlington Raceway with the Cook Out Southern 500, a track known for its demanding nature. Berry has shown he can succeed on tough circuits like Darlington, having earned a third-place finish there last spring while driving for Stewart-Haas Racing, reinforcing his potential to thrive under pressure.
A Gritty Approach to Making NASCAR Dreams Reality
Coming from humble beginnings—washing cars and working on race teams—Berry understands the value of perseverance and teamwork in reaching the highest levels of motorsport. His rookie season in the Cup Series has already produced a historic victory, and as the playoffs commence, he faces the ultimate test of sustaining momentum while competing against NASCAR’s elite.
Berry’s story underlines the demanding nature of the Josh Berry NASCAR Cup challenge, showing that talent alone is not enough. Success at this level requires relentless dedication, adaptability, and acceptance of the many outside factors that can influence results. His journey inspires hopeful drivers who aspire to break through in one of racing’s toughest arenas and hints at exciting possibilities for the remainder of the season.
