Jason Sides looks the part of a dirt racer. His long hair is often pulled back in a ponytail, white-rimmed sunglasses are on his head and his goatee greets you head-on. He takes drags off his cigarette as he works on his car. He personally drives his hauler track to track, a staple of the grassroots racer.

What Sides does though is far from grassroots. In fact, it is quite the opposite, as he competes every single weekend against the best Sprint Car drivers in the country with the World of Outlaws.

But while he does it differently, Sides himself still fits in that category of the very best. He’s a 15-time winner on the World of Outlaws circuit, who has been racing Sprint Cars in some capacity since the early 1990s.

Among his Sprint Car wins across a variety of sanctions are the prestigious King’s Royal at Eldora Speedway, a triumph at Volusia Speedway Park in the DIRTcar Nationals during Speedweeks and a popular victory close to his Memphis-area home in the Short Track Nationals at Little Rock’s I-30 Speedway.

Sides, 44, is a native of the Memphis suburb of Bartlett, Tennessee, and he knows how to do a lot with a little.

“There’s places I know that we’re decent, that we can run good at,” Sides says of his philosophy. “There’s [also] places that I don’t really care for so I know just to go in there and make the show, make the best of it and then get out and try not to tear anything up. Then there’s places where we’ll contend for the win. So, you just kind of have a different mindset at different racetracks.”

Clearly Sides is a thoughtful racer who is mindful of the budget required to make it the entire 94-race Outlaws schedule. But not only is he smart, while possessing superb reflexes, he is also known to have some of the best eyesight in the business. During this year’s Outlaw Showdown at the Dirt Track at Charlotte for instance, he stopped during pace laps in turn two to point out to officials a pair of eyeglasses on the track.

Yet despite his obvious talents in Sprint Cars, Sides didn’t initially have his sights set on the discipline. His career actually began on two wheels, starting out on BMX bicycles and making the move to dirt bikes when he was 13, winning multiple championships.

He raced dirt bikes for about 10 years early in his life, following in the footsteps of his parents.

It was his older brother Paul who got Jason into Sprint Cars. Paul first got a Sprint Car of his own in 1992, while the Sides family operated the dirt track at Memphis Motorsports Park. Paul let his brother sample his car and Jason was instantly hooked.

“One night he let me drive his car and it was just a new adrenaline rush,” Sides remembers. “It was kind of fun and it had a roll cage. I was getting older, kind of old for the dirt bike scene so I got into the Sprint Car and loved it. So I started to sell the dirt bikes and got a Sprint Car.”

Not only did Sides race at Memphis Motorsports Park, he and his brother also prepared the track for the four years the family ran the facility.

“He graded, I watered,” Sides remembers.

He began racing full-time in 2001 and has been a nearly constant and large presence on the World of Outlaws Craftsman Sprint Car Series ever since. He earned the longstanding nickname “Double Down” his first year on the tour, playing blackjack at a bar in Fargo, North Dakota, when the buy-in was five dollars a hand. Sides won on nearly everything he played, longtime series announcer Johnny Gibson took note and one of the sport’s most enduring nicknames was born.

Sides stands out in other ways, too. Ask the driver for an autograph in recent years and you were likely to get a signature from a red Sharpie, as opposed to the black offered up by most drivers.

“Now it’s gone to blue,” Sides says of his unique writing tool, which matches his car’s primary color this year.

“Most people have got black, so if you’ve got something different you stand out. It’s just a way to be different.”

It’s easy to root for Sides, both for his quirks and his roughneck, underdog image, aside from his talent on track. He’s worldly though, having experience running a race team, traveling all over the country and even competing with his Sprint Car brethren in Australia.

“It might be a little bit bigger in Australia as far as the fan turnout,” Sides says about the racing on the other side of the world. “They don’t have as many races as we do, but they still have a 12- or 18-race series. And they have big races like the [Grand Annual SprintCar] Classic and the Scott Darley Memorial. For those few big races, people come out in big numbers.”

Australian Sprint Car racer Shane Finch joins Sides for part of the year each season, and the duo have now been together for a dozen years. Paul Sides also joins his brother on the road for some stretches every year. Often though, Sides rolls into the track alone, having called ahead to have area crew members help on the car each week.

Sides admits that he’s thought about slowing down or changing his role, and he says the travel can be grueling, but for the most part, he loves what he’s doing as much as ever.

“If I find a young driver that’s ready to get out there and do it I might step out and put him in the car or something,” Sides says. “But I don’t see that being any time soon. It might be the end of this year, might be next year, might be three or four years, I don’t know. I’m still having fun.

“I still enjoy working on them and doing a lot of the stuff. Just going up and down the road a lot gets kind of tiring, but that’s part of it. We’ll just see how long it lasts.”