[9][12] Earnhardt Jr. attended the high performance driving school run by Andy Hillenburg[13] and began his racing career at the late age of 17 with his father, competing in the Street Stock division at Concord, North Carolina's Motorsport Park.

Earnhardt played a part in recreating one Winston Cup milestone in 2000 when he competed with his father and half-brother Kerry in the Pepsi 400 at Michigan International Speedway.

In October, Earnhardt Jr. took his second restrictor plate win as he won the EA Sports 500 at Talladega, for which he also scored a Winston No Bull 5 $1 million bonus.

On July 18, during the summer off-weekend, Earnhardt crashed a Chevrolet Corvette C5-R during a practice for the American Le Mans Series Grand Prix of Sonoma at Infineon Raceway.

In 2006, during the spring weekend at Talladega Superspeedway, Earnhardt and other DEI drivers drove with special black paint schemes on their cars, reminiscent of his late father's famous No.

At Indianapolis Motor Speedway, Earnhardt and his crew made a critical decision to stay out on the final pit stop to get a much needed Top 10 finish to move him up to 10th in the points.

[citation needed] Earnhardt began the 2007 NASCAR Nextel Cup Series season by finishing 32nd at the Daytona 500 as the result of a late race crash.

Jeff Gordon, Jimmie Johnson, Greg Biffle, Mark Martin, Ward Burton, Denny Hamlin, Casey Mears, Shane Huffman and Bill Elliott also changed their paint schemes for the occasion.

Earnhardt expressed that his decision was based entirely on his desires to achieve his career goal of a Sprint Cup Championship, and his apparent belief that he would not be able to attain that objective while driving for DEI.

[40] At Michigan, Earnhardt broke his 76-race winless streak, managing to stretch his fuel mileage enough to allow him to win under a caution on the last lap of a green-white-checkered (overtime) finish.

Earnhardt's poor performance continued as he finished 40th at the Coca-Cola 600 due to an ill-handling race car, after which Tony Eury Jr. was fired as his crew chief on May 28, 2009.

Lance McGrew was named interim crew chief starting with the June 2009 race at Pocono, with team manager Brian Whitesell calling the shots at Dover the previous week.

On February 13, 2010, while running in the front of the pack at the Daytona Nationwide Series race, Earnhardt was caught up in a multi-car wreck, causing his car to flip upside down on the backstretch.

Earnhardt enjoyed a hot start to the year, qualifying well in the season's first two months and winning the pole for the spring race at Atlanta Motor Speedway in March.

At the 2012 Quicken Loans 400 at Michigan, Earnhardt dominated the race, leading 95 laps, and won, snapping a 143-race winless streak, almost four years to the day after his last win on June 15, 2008.

At Watkins Glen, Earnhardt had a steady Top 10 going in the final laps but a late race spin resulted in a 28th-place finish, this would drop the 88 team from 1st to 4th in the points.

Earnhardt, Ryan Newman and Kasey Kahne also escaped engine difficulties that plagued Jimmie Johnson, Jeff Gordon, and Tony Stewart.

The following week at Phoenix, he led for 47 laps but was shuffled back in traffic during a cycle caution flag pit stop, which allowed Carl Edwards to assume the lead while Junior finished in fifth place.

At Fontana, Earnhardt started mid-pack and after a couple of mistakes including a lengthy pit stop caused by missed lug nuts on a right rear tire, he came home in 2nd-place finish, assuming the points lead as a result of Brad Keselowski going off pace and falling back.

During the regular Daytona Winter test in January, it was announced that crew chief Steve Letarte would step down from the pit box after the season to become a full-time member of the upcoming NASCAR on NBC broadcast team, alongside Jeff Burton and Rick Allen.

After being repaired and falling to the back of the lead lap, Earnhardt made several charges through the field to salvage a 12th-place finish, keeping him at 2nd place in the points.

Despite struggling at the 3/4-mile track, Earnhardt seeded third in the Chase grid, behind series leader Brad Keselowski, and tied with Jeff Gordon, Jimmie Johnson, and Joey Logano for 2nd place.

At Dover, despite falling back at a few points, Earnhardt Jr. was locked in a battle with Jamie McMurray for control of the final transfer spot into the Contender Round.

Earnhardt started the 2016 season with a crash in the Sprint Unlimited on lap 23 when Brian Vickers cut down a tire and hit him, damaging the side of his car.

On April 20, 2022, Earnhardt won on his debut in the iRacing MOONCAR series, racing vintage 1987 Winston Cup stock cars at Talladega in dramatic fashion, flipping across the start/finish line.

JR Motorsports also has a very successful regional late model program, with Josh Berry capturing the 2012 Motor Mile Championship in the Whelen All-American series.

[94] On January 9, 2023, a consortium consisting of Earnhardt's DEJ Management, Jeff Burton Autosports, Inc., Kevin Harvick Incorporated, and Trackhouse Racing Team purchased the CARS Tour.

His production company Hammerhead Entertainment also assisted in creating a DirecTV special called "Fast Lane For Fun", in which Earnhardt's Whisky River was shown in one episode.[when?]

[98] In 2013 Earnhardt made an appearance on the show Fast N' Loud where he requested Richard Rawlings from Gas Monkey Garage to build him a custom-built car for a road trip vacation.

[127] In May 2012, Earnhardt singled out Republican Representative Jack Kingston of Georgia while speaking against an amendment to a defense bill that would prohibit the military from funding sponsorships in professional sports.