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He is also the grandson of both NASCAR driver Ralph Earnhardt and stock car fabricator Robert Gee, the brother of Kelley Earnhardt-Miller, the half-brother of former driver Kerry Earnhardt, the uncle of driver Jeffrey Earnhardt, the stepson of Teresa Earnhardt, and the older half-brother of Taylor Nicole Earnhardt-Putnam. His first race car was a 1979 Monte Carlo that he co-owned with his older half-brother, Kerry Earnhardt.
Earnhardt's success at Daytona International Speedway throughout his career has earned him the nickname "Pied Piper" of Daytona. By age 19 after two seasons of driving Street Stock Division, Earnhardt had honed his driving abilities to the point of joining the Late Model Stock Car Division.
He struggled for most of the race, and was at points a half-lap down, only catching back up to the pack through a caution.
The win was controversial because with 5 laps to go, it appeared that Earnhardt went below the yellow line to gain position, but NASCAR ruled that Matt Kenseth had forced him below the line, making it a clean pass.
Later in the season, Earnhardt made a comeback, beginning with an emotional win at the Pepsi 400, which was also the first race held at Daytona since his father's death.
Earnhardt had the dominant car of the race, leading 115 out of 160 laps.
His father had crashed in turn 4 after Sterling Marlin made contact with his left rear bumper. shot up the track into the outside wall behind Waltrip and his son and collected Ken Schrader in the process. was pronounced dead at pm due to a basilar skull fracture.His primary competitor for the award was Matt Kenseth.Kenseth outran Earnhardt in the season-opening Daytona 500.Also in 1999, he drove in 5 Winston Cup races in the No.8 Budweiser-sponsored Chevrolet for Dale Earnhardt, Inc., and then in 2000, he went full-time in the Winston Cup series.