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Dale Earnhardt Letterman YouTube: Late Show with David Letterman
YouTube: Late Show with David Letterman

On February 15, 1998, Dale Earnhardt Sr. finally won the Daytona 500 after 20 years worth of unsuccessful runs. By that time, he already had all his seven NASCAR Cup Series championships under his belt, but that fateful day in ’98 would mark Earnhardt’s first, and only, victory in the Great American Race.

Now, Earnhardt may have earned his Intimidator nickname because of his aggressiveness on the track, but that didn’t keep the NASCAR Hall of Famer from having a great sense of humor. Even at his own expense.

In this segment from the Late Show with David Letterman that aired on CBS shortly after his big victory, Dale Sr. shared the 10 reasons it took him 20 years to win the Daytona 500. Earnhardt jokingly listed off some important race-winning tricks he learned, such as disengaging the emergency brake and getting his 300-pound cousin “Ricky” to let him drive solo.

Earnhardt’s tongue-in-cheek secrets to success also covered race car driver etiquette (flipping the bird more), tips on the stock car’s gas pedal (use it), and the importance of not training with the Canadian snowboarding team (which, if you remember, famously got busted for smoking weed after winning the gold medal in the 1998 Nagano Winter Olympics).

WATCH: Dale Earnhardt on Late Show with David Letterman

Read More: Ryan Newman, Martin Truex Jr., Chase Elliott, and Other NASCAR Drivers Give Their Hottest Moon Landing Takes at Daytona International Speedway

Watching the late night segment is pretty bittersweet, considering Dale Sr. is cracking jokes about the race where he would lose his life just a few years later. Every NASCAR fan remembers that the driver of the iconic No. 3 Chevy died instantly in a collision with Sterling Marlin during the final lap of the 2001 Daytona 500. That tragic Cup Series race at Daytona International Speedway rocked the foundation of the sport and continues to resonate in NASCAR.

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Despite the ultimate sadness surrounding the Daytona 500 for the Earnhardt family, it’s nice to look back and see Dale in such good spirits following one of his many legendary NASCAR wins.

This post was originally published on December 12, 2017.

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