– When Tony Stewart makes his way to Talladega Superspeedway for the Alabama 500, Oct. 23, it will mark the end of an era. It will be the final race around the 33-degree high banks for the driver retiring at season’s end who has definitely had a “love-hate” relationship with the mammoth venue.

From the first time he competed at NASCAR’s Most Competitive track, Stewart served notice that he would be a threat to win each time he climbed behind the wheel.

As a NASCAR Sprint Cup rookie in 1999, the Columbus, IN native came to the 2.66-mile venue where he started eighth, led 10 laps and came home fifth behind some of Talladega’s best ever – Dale Earnhardt, Dale Jarrett, Mark Martin and Bobby Labonte.

During his first 15 NASCAR Sprint Cup Series races at the biggest and baddest track on the planet, he was a constant frontrunner, recording six runner-up finishes and 14 top-10 results. In fact, his six second-place efforts came in an 11-race stretch.

“Anytime you can finish in the top two here it is like a win,” said Stewart in 2006 after tying Buddy Baker as the track’s leader in bridesmaid finishes. “As volatile as this place can be with getting in a wreck and this or that, for us to say in the last 11 races that we’ve finished second six times is something in all reality to be proud of because this is not a race track that you can do it all on your own. So to be able to get second, I feel like we have a lot to be proud of.”

The year 2008 ended up being special for Stewart at Talladega. Starting that spring from the pole position, he won the NASCAR XFINITY Series race, then continued his prowess in the fall with his first – and only – NASCAR Sprint Cup Series win in the Alabama 500. To say he was happy was an understatement.

“It’s one thing to get back to victory lane, but to do it at Talladega, people don’t understand what that means,” said a jubilant Stewart in Gatorade Victory Lane. “This is one of a few tracks I haven’t won a Cup race at and talk about one to win. I’ve wanted to win here for so long. It was very important for me to win here. Winning the (XFINITY) race this year was huge to me. Now winning the Cup race, somebody is going to lose their vocal cords of how happy they are. Man, it’s just an awesome feeling to finally win here. We finally had one of those days where everything went right for us. I have so many friends down here (in Alabama) – Red Farmer and Donnie Allison (both of the famed Alabama Gang) and all these fans.”

Since that triumph, however, the driver of the No. 14 Stewart-Haas Racing Chevrolet has struggled with only two top-10 finishes. One of those came in this past spring when Ty Dillon was called upon to relieve Stewart after he started and ran the car until the first caution period.

His best shot at another Talladega win went awry on the last lap in the 2012 fall race when he, while leading, made contact with Michael Waltrip in between turns three and four, igniting a 25-car pile-up. “A mistake on my part,” Stewart said that day. “I was trying to win.”

His philosophy, however, remains the same at the 33-degree banked venue.

“It’s the same (philosophy) as it always has been….drivers knowing what to do and knowing what to look for with their car,” said Stewart at Talladega in May. “It’s learning what their cars can do in practice and how to pass. Some have figured it out - to get your car with momentum without the car stalling out. Then, hope to avoid trouble.”

Overall, the three-time NASCAR Sprint Cup Series Champion’s resume is a good one at Talladega. In 34 NSCS races, in addition to his lone victory and six runner-up results, he has 14 top-10 finishes and has led 328 laps in 21 races. He has finished on the lead lap in 22 events. His best start is second on two occasions.

So, how will the final chapter of Stewart’s novel on Talladega turn out? Could it be something right out of a Hollywood script with a long-overdue victory? Maybe, but he’ll have 39 other drivers who will want to write their own piece of Talladega history.

Talladega Superspeedway’s action-packed weekend kicks off on Friday (Oct. 21) with practice sessions for both the fred’s 250 Powered by Coca-Cola NASCAR Camping World Truck Series (NCWTS) race and the Alabama 500. Saturday’s schedule includes qualifying for the NCWTS fred’s 250 Powered by Coca-Cola (9:30 a.m. CDT), the fred’s 250 Powered by Coca-Cola (the Round of 8 Elimination race in the NCWTS Chase), which gets the green flag at 12 Noon CDT, and Foodland/Food Giant Qualifying for the NSCS (3:00 p.m. CDT). Sunday’s Alabama 500, which will see the field of 12 contenders for the title be reduced to eight at the checkered flag, is set for a 1 p.m. CDT start on Sunday, Oct. 23.