If there are three things that describe Jason Sides, it’s a pony tail, a constant smile and a post-race beer or two — or five.

The 46-year-old who has spent his entire life based in his hometown of Bartlett, Tenn., is a fan favorite because of his demeanor. Not only is he easy to talk to, Sides looks just like that guy who sits in front of you in the grandstands that knows everything there is to know about sprint car racing.

The difference is that Sides has been in the driver’s seat for more than half of his life, dedicating himself to a passion that has left him broke, divorced and flat out tired.

“I wish I would have saved some money, but I don’t have any regrets,” he said. “I’m glad I’ve done what I’ve done. It’s a lot of work, a lot of time traveling. You miss your family a lot. As far as the career part of it, I’m glad we got to do what we did because not everybody can do that.”

Sides is in a transition as his success has waned in recent years. No, the pony tail isn’t going anywhere, but his role is beginning to change. While Sides continues to be the car owner, crew chief, racer, truck driver and maintenance and tire overseer among other things, he notes his time behind the wheel is coming to a close.

“I feel like we’ve been with the Outlaws, because I’m counting 2001 and ’02, for about two decades,” he said. “Maybe one more year for myself, making it a nice, round number of 20 years on the road. Then maybe another 10 or 20 years with someone else in the car.

“I don’t want a job. It’s still a job, but if you can have someone come in and have good runs and make good money you don’t have to work for somebody else. I’ve thought about going home and being a forklift driver. Then you’re working for someone else; be there at a certain time, go to lunch at a certain time. I sleep in, get up late, drink beer. It’s either this or something that’s in this neighborhood of our lifestyle is the only thing I’ll be able to do.”

Sides spent the 2001 and ’02 seasons as a full-time competitor on the World of Outlaws Gumout Series, winning the rookie-of-the-year award with both the series and the National Sprint Car Hall of Fame in 2001. He became a full-time World of Outlaws NOS Energy Drink Sprint Car Series driver in 2003, capturing top rookie honors. He’s spent nearly every year since as one of the regulars with The Greatest Show on Dirt.

Sides previously put in his time in the 360 winged sprint car ranks. He shifted from motocross to sprint cars in 1993 and ran close to home for a few seasons before hitting the road to compete on the ASCS National Tour in the mid 1990s. Sides finished in the top 10 in the championship standings five times, including a career-best third in 1997. He also won the Short Track Nationals and Ronald Laney Memorial King of the 360s in 2000 and ’01, respectively, before transitioning into 410 winged sprint car competition.

Sides entered this season with 15 World of Outlaws feature triumphs, most notably the 2004 Kings Royal at Ohio’s Eldora Speedway. That came the season following his first full campaign with the World of Outlaws, which yielded a sixth-place result in the standings. He’s accomplished a top-10 finish in the standings eight times, led by career-best fifth-place performances in 2009 and ’10. Sides’ most WoO wins in a single season were four in 2011.

However, it hasn’t always been smooth sailing for Sides. He was one of the drivers who elected to leave the World of Outlaws for the National Sprint Tour in 2006.

“We were at Eagle Raceway (in Eagle, Neb.) in 2005,” Sides said. “(World Racing Group Chief Executive Officer) Brian Carter is walking around with an open checkbook paying people to stay with the Outlaws. Not that I had my mind made up, but I probably did. Brian never came to me with an open check asking, ‘Are you going to stay with us?’ I had a bad taste in my mouth so we went to the NST. Every team that was with the NST was more than willing to do things for the sanctioning body. If Fred (Brownfield) needed me to put my car on display at a Walmart, we did it no questions asked. There were some things that when the Outlaws asked you to do something it seemed a little different.

“The NST was a big family,” Sides recalled. “We all had fun racing together. Everybody helped everybody and it was not us against them. I even ran a few Outlaws shows that year in the Doyle’s Harley-Davidson car. When I put that big NST sticker on it and was quick time at Silver Dollar Speedway (in Chico, Calif.), they disqualified us because they said we were too loud or something. I think there were some politics in it. I think if Fred wouldn’t have been killed it would have kept going or somehow merged together. Fred was too good of a promoter. When he died we continued on without the leader, we finished the races. We had a banquet. After that the wind was out of the sails.”