With the privilege of hindsight, it’s easy to say that the 2000s were a great era for NASCAR fans. Thrilling races or battles could never have been too far away when you had legends of the ilk of Dale Earnhardt, Jeff Gordon, and Tony Stewart stepping up to fight each other.

There was no dearth of great drivers in that era. While the headlines were largely in favor of Gordon and Earnhardt, their tales had other major characters too. Add Bobby Labonte, Dale Jarrett, and Mark Martin to the mix and you know how storied that epoch was.

Tony Stewart was very intimidated by The Intimidator

4 years after his retirement, Stewart sat down with Michael Waltrip in 2019, on his Waltrip Unfiltered Podcast. They discussed a lot of different topics, one among which was Dale Sr. “I always like to talk about my buddy Dale,” stated Waltrip. “What’s the first time y’all crossed paths and was it friendly or was it not?” he chuckled.

Peering through the years of NASCAR he has in his head, Stewart recalled “Well, actually, I think because of Coca-Cola and the fact that we were a part of the Coca-Cola racing family… I think that was the first time we really got to meet Dale, and that was at a production day photo shoot. So it was before we even got on the race track together.”

Stewart was obviously very scared of meeting The Intimidator. He told Waltrip, “But he… it was crazy. Because I’m like ‘This guy is not even gonna know who I am. He’s gonna wonder why am I even here on this day.’ For him to know what my background was in racing and say that he’d seen me race just was amazing to me.”

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Dale Sr. was fittingly given that nickname, but that fear broke soon. It came in the way of some great advice.

Dale Sr. shared secrets for a good happy hour

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Stewart shared with Waltrip how happy hour sessions were always bad for him. “​I’d go out in the first practice and my car was good. And then we’d run happy hour and it was like somebody snuck in there, stole my car, brought another car that looked just like it. It was totally different,” is how he remembered those sessions.

But that changed at Darlington. After a good qualifying session and practice session, it was the same rigmarole. Then, “And I got out, I was mad, I’m yelling at Greg Zipadelli and we’re arguing with each other. And all of a sudden, BAM! I get hit in the side of the head.” 

With all the anger Stewart already had in his chest, this was only going to make things go from bad to worse. He remembered, “But what it was was a chunk of rubber the size of a baseball. And Dale had scraped the rubber from the underside of the hood, and made a ball and hit me on the head with that thing. The rubber all blew apart.” 

“And I’m looking… I’m looking to kick somebody’s a**, I mean I’m ready to fight. I turn around and it’s Dale and it’s Chocolate and those guys… they’re all laughing and carrying on. He was laughing at me and he goes ‘I don’t know what it is but I know it’s not that bad.’ It was that that got me calmed down,” he revealed.

“At the end of it, he goes ‘Hey every happy hour session is an unhappy session. You’re never gonna be happy in happy hour. So just calm down, it’ll be fine.’ And I think he ran second the next day, and I ran fourth. So it wasn’t that bad after all. But he was right, he said “It’ll be better tomorrow.”

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Inside all that steely exterior that led to the nickname Intimidator, Dale Sr had a softer side. He had seen it all, done it all. For a relative newcomer to the scene like Stewart, words from Dale must have been priceless.