Very few NASCAR drivers can be compared to the late Dale Earnhardt Sr.

Despite his seven Cup Series titles, the NASCAR legend only won the Daytona 500 – the Super Bowl of NASCAR – once in his more than two decades at the sport’s highest level. And it took him 20 years to do it.

After his 1998 Daytona 500 win, Earnhardt paid a visit to The Late Show with David Letterman – the now-former host is also an IndyCar Series team owner – to have a little fun with his winless record in NASCAR’s biggest race, listing off the top 10 reasons why it took him 20 years to finally win.

And since this video was floating around NASCAR Twitter this week, in part, thanks to Dale Earnhardt Jr. retweeting it, we thought it’d be great for #TBT.

Although many of Earnhardt’s reasons are tailored to the late 90s – like the Spice Girls and the Olympic Canadian snowboarding joke – it’s still pretty funny to watch him poke fun at himself.

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