Waltrip was hired by Dale Earnhardt to drive his team's new No. 15 NAPA Auto Parts-sponsored Chevrolet Monte Carlo entry, Waltrip drove for Earnhardt in the Busch Series in 1989 and 1994. In his first race with the team, the 2001 Daytona 500, Waltrip broke his streak of 462 consecutive Cup races without a victory and won his first career points-paying Cup race. His teammate Dale Earnhardt Jr. finished in 2nd. However, the win itself was largely overshadowed by Earnhardt, Sr.'s fatal crash on the last lap. In the movie "The Day: Remembering Dale Earnhardt", Waltrip said that Earnhardt let him in line late in the race, which allowed him to take the lead, noting that Earnhardt "never let anyone in line". This presumably is because Earnhardt wanted Waltrip and Earnhardt Jr. to finish in the Top 2 spots, as both were members of his team. Waltrip was not aware of the severity of Earnhardt's crash until over 30 minutes after the end of the race when he was celebrating in victory lane. Ken Schrader, after having been treated and released from the infield care center following the crash (his car was hit by Earnhardt's during the crash), informed Waltrip that Earnhardt had been taken to Halifax Medical Center, from the speedway, where Earnhardt was pronounced dead at 5:16 PM EST.