Early career and late model racing Berry met his future car owner
Dale Earnhardt Jr. in 2008 when competing in an online sim racing league called DMP Online Racing. At the time, he was racing
Legend Cars at his home track of the
Nashville Fairgrounds Speedway in
Nashville while also attending
Volunteer State Community College and working as a bank teller to fund his racing career. Earnhardt Jr. then signed Berry to his
JR Motorsports team in 2010 to compete in
late model racing. At the 2015
Denny Hamlin Short Track Showdown, Berry spun
Lee Pulliam while racing him and
Timothy Peters for the lead on the final lap; Berry was moved down to seventeenth in the running order and drew criticism from Pulliam, who called Berry "the biggest joke in racing." After being spun by
Bobby McCarty in
CARS Tour at
Motor Mile Speedway in 2019 and
Ace Speedway in 2020, both times when Berry was leading the race, Berry intentionally wrecked McCarty later in the Ace Speedway race, resulting in a one-race suspension. Berry ditched a planned CARS schedule and instead focused on the
NASCAR Advance Auto Parts Weekly Series, winning 24 races en route to a national championship. On August 31, 2022, Berry was the crew chief for
Dale Earnhardt Jr. in the
CARS Tour Window World 125 late model race at
North Wilkesboro Speedway and on May 17, 2023, again for the race at North Wilkesboro Speedway the following season.
NASCAR and ARCA 2014–2021 Berry's first
NASCAR Xfinity Series race came at
Iowa Speedway, driving the No. 5
Chevrolet Camaro for
JR Motorsports. He started tenth and finished twelfth, finishing on the lead lap. He returned to the 5 car for the season finale at
Homestead-Miami Speedway, again logging a lead-lap finish in 25th. He finished his debut season 50th in points. He returned to JR Motorsports for one race in 2015, finishing seventh at
Richmond International Raceway. In 2016, his first race of the season was at Iowa, where he finished ninth in the No. 88 for JR Motorsports. He returned to that car in the first race of the Xfinity Series Playoffs, at
Kentucky Speedway and ended up finishing thirteenth. Berry also made one start for
Obaika Racing, finishing 27th at
Darlington Raceway. Berry also debuted in the
NASCAR Camping World Truck Series during the
2016 season, driving the No. 71
Contreras Motorsports truck to a thirteenth-place finish at
Chicagoland Speedway. In
2017, Berry made his first Xfinity Series start of the season, attempting the
Kansas race for newly-formed
NextGen Motorsports, driving their No. 55
Toyota. After qualifying 33rd, he finished 34th after suffering an engine failure on lap 182. In 2018, Berry made his debut in the
ARCA Racing Series, driving for
Chad Bryant Racing in their No. 22
Ford at
Salem Speedway in April of that year, finishing fourth. In 2019, he drove for Visconti Motorsports and finished third in their No. 74 car in the
NASCAR K&N Pro Series East race at
New Hampshire in September, which was his first start in that series. These were his only starts in NASCAR or ARCA in both of these years.
2021 at Atlanta in 2021 (No. 18) and
Jeb Burton (No. 10) at
Atlanta in March 2021 On October 22, 2020, JR Motorsports announced that it had scheduled Berry to drive its No. 8 car for 12 races in the
2021 NASCAR Xfinity Series season. At
Phoenix Raceway, Berry was turned by
Santino Ferrucci, prompting him to give Ferrucci
double middle fingers as he drove by. He recorded his first Xfinity win at Martinsville upon passing
Ty Gibbs for the lead with 28 laps remaining; Berry was the fifth driver to win his maiden race in the series at Martinsville alongside
Sam Ard (1982),
Brett Bodine (1985),
Brad Teague (1987) and
Jeff Burton (1990). In March, Berry returned to the Truck Series for the first time since 2016. He substituted for
Kris Wright in the No. 02 for
Young's Motorsports after Wright tested positive for
COVID-19. In May, Berry made his
NASCAR Cup Series debut in the
Drydene 400 at
Dover International Speedway, substituting for
Justin Haley in the
Spire Motorsports No. 77 car after Haley was sidelined by
COVID-19 protocols, marking the second time that Berry was called on to fill in for a driver that had to miss a race because of COVID-19. He also drove in his second
ARCA Menards Series East (formerly NASCAR K&N Pro Series East) race that weekend in the No. 41 for
Cook-Finley Racing, which meant that he did triple duty that weekend at Dover. On May 26, it was announced that Berry would get to compete in the Xfinity Series race at
Mid-Ohio road course in the No. 31 for
Jordan Anderson Racing.
Miguel Paludo was driving Berry's normal car, the No. 8 for JR Motorsports, in this race. Another Truck return came in June in the No. 25 of
Rackley W.A.R. for three races at Texas, Nashville, and Pocono after the departure of
Timothy Peters. A month later, he rejoined JRM for the Xfinity race at Loudon in the No. 1 after
Michael Annett suffered a leg injury. On August 16, Berry was confirmed to drive the No. 8 for JR Motorsports full-time in 2022. Later in the week, he filled in for Spire's other Cup driver
Corey LaJoie at Michigan when LaJoie was not allowed to compete due to COVID-19 protocols. When Annett was re-injured in September, Berry once again took over as replacement at Bristol and Las Vegas, and he won the latter after passing teammate
Justin Allgaier with under twenty laps to go.
2022 Berry began the
2022 season with a sixteenth-place finish at
Daytona. He scored wins at
Dover and
Charlotte to make the playoffs. During the playoffs, Berry won at
Las Vegas to make the Championship 4. Berry would ultimately finish fourth in the final points standings.
2023 During the
2023 season, Berry drove winless but stayed consistent enough to make the playoffs. He was eliminated at the conclusion of the
Charlotte Roval race. On March 3, it was announced that Berry would run the
Hendrick Motorsports No. 9 at the
Las Vegas Cup race after
Chase Elliott sustained a leg injury from snowboarding in Colorado. Berry finished 10th the following week in the Cup Series race at Phoenix, and filled in for the next three oval races until Elliott recovered to return at Martinsville. Berry finished second at
Richmond, his career best in the Cup Series up to that point. On April 26, Berry was announced as the substitute driver of the No. 48 after
Alex Bowman suffered a back injury from a sprint car racing accident. On May 21, he raced in the
2023 NASCAR All-Star Race in place of Bowman, qualifying first place in the open qualifying race, allowing him to compete in the main race, where he finished fifteenth. He would then be announced as the driver for
Legacy Motor Club in the No. 42 at
Michigan after
Noah Gragson was suspended indefinitely. He would go on to finish 34th after being involved in a crash while running sixteenth.
2024: Stewart–Haas Racing in 2024 On June 21, 2023,
Stewart–Haas Racing signed Berry as
Kevin Harvick's replacement in the No. 4 in
2024. Berry started the season with a 25th place finish at the
2024 Daytona 500. He scored a season-best third-place finish at
Darlington and
New Hampshire. On May 28, 2024, Stewart–Haas Racing announced it would shut down its NASCAR operations at the end of the season. In the Xfinity Series, Berry signed to drive the
AM Racing No. 15 at
Pocono. During the
2024 Coke Zero Sugar 400, Berry was involved in a major crash on lap 159. While leading the second lane down the backstretch,
Austin Cindric was turned up the track following a push from behind. Cindric and Berry both spun towards the inside as a multi-car incident ensued behind. Berry's car lifted off the ground, overturned, and slid on its roof at high speed for several seconds. Still upside down, it impacted the inside wall head-on, sending it into a spin before it finally stopped on the apron of the track. After track safety workers righted the overturned car, Berry exited unharmed. Thought of a very similar nature arose to a crash suffered by
Ryan Preece in
the previous year's running, Berry's car did not barrel roll, due likely to the updates to the track following the former's incident that saw the grass in the area removed and replaced with pavement. The flip happened in spite of an additional air deflector implemented in the intervening week after Corey LaJoie had a similar crash at Michigan the previous race, intended to prevent cars from lifting off the ground.
2025: Wood Brothers Racing, first career win, and playoff collapse at
Las Vegas Motor Speedway On July 3, 2024, Berry signed a multi-year deal with
Wood Brothers Racing to drive the No. 21 car, replacing
Harrison Burton. He started the
2025 season with a 37th place DNF at the
2025 Daytona 500. About a month later, with a fourth-place finish, it was the first time that the Wood Brothers finished inside the top five at
Phoenix. The next week, Berry scored his first career Cup Series win at
Las Vegas after passing and pulling away from
Daniel Suárez. This win marked the first time since the
1986 and
1987 seasons that the Wood Brothers won in back to back seasons (both won with
Kyle Petty). After a string of back-to-back-to-back last place finishes at
Darlington,
Gateway, and
Bristol, Berry was eliminated at the conclusion of the round of 16. ==Personal life==