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Sunglasses or Mustaches: These are the COOLEST Drivers in NASCAR History

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Kauy Ostlien

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What makes a NASCAR driver cool? Is it a nickname, a facial feature, an on-track ability, or sheer will to win? While there is no set definition of a cool driver, there have been many who fall into this category in the history of NASCAR.  Some come straight to fans’ minds, and some may be overlooked.

Richard Petty

It wouldn’t be a NASCAR list of any variety without a mention of the King. Richard Petty raced for 35 seasons and won 200 races. He also ran in every Daytona 500 until 1992, winning seven of those to complement his seven championships.

On the track, he was different from the others. Petty was known for his Petty Blue 43, a bright shade of blue that stood out in the large fields of yesterday. Unlike other drivers, he wouldn’t keep a water bottle in the car. Instead, a wet rag would be found in the mouth of the king. He also set the standard for NASCAR drivers’ tough-as-nails, cowboy mentality, whether it was the numerous broken bones he had in his career or fighting age to keep racing well into his 50s. Petty always managed to emerge, wet rag in mouth, ready to start the next race.

While the on-track accolades only add to the King’s coolness. Richard Petty also set the model for a driver off the track, whether he was signing every autograph he could, appearing in movies such as the Cars franchise, or being an ambassador for the sport at every opportunity.

Petty’s off-track personality has consistently been shown in his style. The sunglasses, ornate cowboy hat, and boots have become synonymous not only with Petty but with NASCAR itself.

His on-track accolades and off-track personality have created an unprecedented level of mystique around the Hall-of-Famer. Celebrities, athletes and dignitaries have all looked in awe when meeting the man behind the hat.

There is not much to say about someone like Richard Petty that hasn’t already been said. The man has no myths about him but is a legend, one that is the idea of cool.

Harry Gant

Being good-looking can make someone cool; for Harry Gant, being good-looking wasn’t just about his appearance; it was a nickname.

Harry could have been known as the “Marlboro Man” of NASCAR. His Skoal Bandit 33 is still a popular throwback paint scheme choice for today’s drivers. He is a member of the NASCAR 50 and 75 Greatest Drivers lists and the NASCAR Hall of Fame. In his time behind the wheel, Harry won 18 Cup Races and 21 Xfinity Series races. However, a keyword in that sentence is time. Gant would race from 1973 to 1994 in the Cup series; while a 22-season career is commonplace in NASCAR, Gant began Cup racing at 33 years old and raced till he was 54.

Not only did he race into his 50s, but he also won in his 50s. Years before Mark Martin did so, Harry Gant won eight of his 18 career Cup races above the age of fifty. Much like Martin, Gant would continue to compete at a high level after his last win. In his last full-time season, Gant would win an Xfinity Series race, adding to the other nine he had won after age 50. After retiring in 1994, the ageless wonder would run a part-time Truck Series schedule in 1996. In that 11-race schedule, Harry would get four top tens, showing he hadn’t missed a step.

You may be saying, “Big deal. NASCAR is chaotic, and anyone can win any given week.” Well, let’s talk about Harry’s other nickname, Mr. September.

In September 1991, Harry entered the month 10th in Cup series points. He would end the month fourth. This was not due to driver consistency or a favorable approach to the old points system but to his four consecutive race wins. In fact, out of the five races that month, the only one he didn’t win, the 51-year-old sat on the pole and led 350 laps before finishing second to Dale Earnhardt.

Sometimes, the old guys can be the coolest. But all the time, a few good nicknames can do the job, too.

Davey Allison

Davey Allison was the next generation of the Alabama Gang, a group made up of individuals such as Bobby and Donnie Allison, Red Farmer, Neil Bonnet, and others. As Bobby’s son, Davey had to grow up in the shadow of one of NASCAR’s first superstars. Even in Davey’s first full-time season in the Cup Series, Davey ran second to Bobby in the Daytona 500. From 1988 to 1990, Davey was in the front half of NASCAR Cup Series Standings. But, by 1991, Davey had secured his spot at the front of the Cup Series. This can be accredited to the addition of America’s Crew Chief, Larry McReynolds. McReynolds had come on board five races into the 1991 season. In that first season, the pair would score five wins for team owner Robert Yates.

Davey being good behind the wheel isn’t why he’s the type of driver to ascend to the level of the “Cool Guys.” It wasn’t the mustache, a trend in this list’s drivers, or the slick black car. It was that he might be the toughest driver to ever hop behind the wheel. The 1992 season is a perfect example of this.

In a season where Davey scored five wins, 15 top fives, and 17 top tens, Davey suffered not one but two crashes that would have typically found him out of the car for some time. However, Davey never missed a start. The first wreck, at Charlotte, found Davey barely winning the race while spinning to the outside wall and headed to the hospital. Beat up and battered, Davey would finish fourth in the following race. The “One Hot Night” race was a success for NASCAR and set the standard for future All-Star races. Unfortunately, this was just the first hospital trip Davey would have in 1992.

The second notable crash was at Pocono, where Davey was found barreling end over end and headed for the infield. Davey would be airlifted from the track and found to have multiple broken bones, including his arm, and a concussion. Davey, bloodshot eyes and all, would start the next race at Talladega before letting Bobby Hillin hop into the 28 to finish the race and maintain Davey’s spot in the standings.

Despite all his work to maintain a good standing in points, even leading into the season’s last race. It wasn’t meant to be. After a crash in the Hooters 500, Davey’s pursuit was over. However, 1993 was looking to be a fresh start for Allison. But 16 races into the season, Davey would pass away after his helicopter crashed at Talladega. Davey’s legacy lives on in the stories of not only how tough he was, but how good of a person he was.

Tony Stewart

To be cool doesn’t necessarily mean you have to look cool. To those who know nothing about racing, Tony Stewart may look normal. But race fans know him as one of the fiercest drivers of the early 2000s. As a young man growing up in Indiana and idolizing A.J. Foyt, Stewart had all the right influence to become one of the “Cool Guys” of the NASCAR Garage.

Stewart won three NASCAR Cup Series championships and 49 races. He also won an IndyCar championship, USAC Triple Crown, two Chili Bowls, Indy 500 rookie of the year, and numerous Hall of Fame inductions. He also attempted the Indy 500/Coke 600 double twice, including a double top-ten finish in 2001. In addition to those accolades, Tony won the 2011 NASCAR Cup Series Championship while driving for himself, the first owner-driver to do so since 1992.  Tony Stewart didn’t drive cars; he drove the wheels off them.

From a deeper level, Tony didn’t just help grow the sport through success on the track. To many, Tony filled the void left by the passing of Dale Earnhardt. Dale was respected on and off the track, the same as Tony. Dale would move you on the track if you disrespected him, and after, maybe he’d let you know what happened. But Tony would take an even more blunt approach to that attitude.

As a driver, owner, and track operator, Tony Stewart was a highlight reel and soundbite machine. Sometimes, he combines the two, such as when he had a post-race altercation with Joey Logano at Auto Club, and subsequently, he tells Steve Burns that he isn’t done with Logano.

Tony always had something to say, whether it was speaking his mind about fellow drivers, NASCAR officials, or even NASCAR’s media. For example, when he told a reporter his true feelings about a press conference question.

Being a cool driver means being able to talk big and back it up. Tony Stewart will always be a stand-out example of this in the sport.

Dale Earnhardt

Who else would round off a list of NASCAR’s “Cool Guys”? No driver has impacted the sport as much as Dale Earnhardt.

Dale’s connection to the fans was immediate; of course, to some, he had been a neighbor or a classmate. The son of a local racing legend, Dale would ascend everything in the sport that was set in front of him.

If you think a nickname makes a driver cool, Dale has the nickname. The Intimidator, a nickname given to a man who sent fear into the drivers who saw the black nose of the three looming behind them. A nickname given to the man behind the sunglasses who would move a driver to win a race and stand up for himself when he felt he was wronged. A nickname that has even ascended the driver, having been used by the Kannapolis minor league baseball team from 2001 to 2019 and a roller coaster from 2010 to 2023.

Earnhardt was also a marketing machine, you want to buy a Coke, Dale’s on the machine. Do you need some new sunglasses? How about a pair of Gargoyles so you can look like the Intimidator? Not only did he prop up these brands, but in some cases, he has become associated with them in pop culture, like long-time sponsors Wrangler and GM Goodwrench.

The personality was even more complimentary of the driver. Could there have been a better combo than the black number three paired with the big mustache and black sunglasses? No driver has a better combination of car, style and personality.

Earnhardt’s cultural impact has carried on even past his death. His merchandise is still scattered across race weekends. His advertisements still hang in bars, gas stations, and garages nationwide. His moves on the track are still legend around the bonfires of the infield.

Legend status is as cool as it gets, but Dale Earnhardt never needed to be a legend to be cool. He was going to be no matter what.


While some are more obvious than others, this is only some of the “Cool Guys” of NASCAR. While fans have their lists, they will never be complete. As the years go on, more and more drivers will try to find a way to become one of the “Cool Guys”.

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Picture of Kauy Ostlien

Kauy Ostlien

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