After driving the No. 8 Chevrolet Monte Carlo for Dale Earnhardt, Inc. (DEI), his father's team in the NASCAR Cup Series, for much of his early Cup career, he moved to Hendrick Motorsports to drive the No. 88 in 2008. He remained with HMS until his retirement as a full-time driver in 2017. Earnhardt retired with 26 wins in the Cup Series, a total that ranks him tied for 30th in NASCAR history (with Fred Lorenzen and Joey Logano) as of November 2020.