dale earnhardt on late show with david letterman after winning 1998 daytona 500
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Dale Earnhardt Showed His Funny Side With His Top Ten List Segment on "Late Night With David Letterman"

The segment possesses an eerie quality to it though.

On February 15, 1998, Dale Earnhardt Sr. finally won the Daytona 500 after 19 failed attempts. By that time, he already had all of 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 The Intimidator nickname because of his aggressiveness on the race track, but that didn't keep the NASCAR legend 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 win, Dale Sr. shared the 10 reasons it took him 20 years to win the Daytona 500. Spoiler alert: one of them involves the Spice Girls.

WATCH: Dale Earnhardt Shines in Late Show Segment

As you can see from the clip, the Late Show writers definitely knocked it out of the park with this one.

In the segment, Earnhardt jokingly lists 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 covers 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).

Clearly, Dale was still buzzing after finally winning the big race that had eluded him for so long. As it turns out, '98 would be a good year for Dale. His son, Dale Earnhardt Jr., had just started his first season as a full-time NASCAR driver in the Busch Series (now the Xfinity Series). Despite a disappointing start at Daytona, Dale Jr. would eventually find his footing and go on to win the Busch Series title, a feat he would accomplish again the following year. You better believe that Dale was proud!

Junior would go on to win two Daytona 500s for Hendrick Motorsports in 2004 and 2014, though sadly Dale Sr. would never get to see those wins. That's what makes watching Senior's late night appearance so bittersweet, considering the fact that he's 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 Chevrolet 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.

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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