Editor's note: This story originally ran in 2019 and is being republished as part of our 2022 Indy 500 coverage. Some references may be out of date, but click here for the latest on the race.

Tony Stewart has often said he can drive anything. But when it came to driving everything on the Sunday of Memorial Day weekend in 1999, he had his doubts.

As IndyCar celebrates the 50th anniversary of Mario Andretti's Indianapolis 500 win, this year also marks the 20th anniversary of Stewart's first attempt, in 1999, to compete in the Indianapolis 500 and NASCAR's Coca-Cola 600 on the same day.

Two races, 1,100 miles. And that's not counting the 575 miles between Indianapolis and Charlotte.

“(Stewart) was real uncertain,” said then team co-owner Larry Curry. “I told him, ‘You can do this and you’re gonna do this,’ but he was unsure of himself.”

Despite those uncharacteristic doubts, Stewart pulled off the grueling double.

Five drivers have attempted to compete in both races in the same day; four have started the races. But Stewart remains the only one to finish both races, doing so in a combined 7 hours, 43 minutes and 42 seconds.

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Tony Stewart 'didn't have a clue'

“I had no idea what I was doing,” said Stewart, who had shifted from IndyCar to NASCAR that season. “Obviously I knew what I was doing driving the race cars. I didn’t have a clue what it was going to take endurance-wise to do both events. I had never done anything with nutrition. I didn’t have the knowledge to know what I needed to know on the nutrition side to take care of myself for those two races.”

ESPN reported at the time that Stewart had just two mini-bagels for breakfast and tried to eat a Power Bar in his car but it melted in the heat.

Time constraints -- an itinerary specified to the minute where Stewart needed to be -- weather and a pit problem added up to a challenge unlike any other in his career.

Stewart’s previous IRL experience came in handy, as the weather and accidents by other drivers limited his track time that year.

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“I was in IndyCar the year before, so it was like putting on an old pair of shoes,” said Stewart. "(There was) precious (little) time to just relax. It was a busy time just going back and forth to Charlotte. I didn’t really do much for those three weeks other than just focus on those two races.”

Stewart had joined Joe Gibbs Racing for the 1999 NASCAR season but his heart never left open-wheel racing. With Curry, his IRL race engineer, by his side, Stewart wanted to make history as the first driver to complete the Indy 500 and Coca-Cola 600 in a single day.

Before the start of the 1999 IRL season, Stewart entered into ownership with Curry and former Menards PR director Andy Card to form Tri-Star Motorsports (no relation to the former NASCAR team with the same name). Stewart and Curry, who by now was a co-owner, began talking early in the 1999 IRL offseason about doing the double.

From fast laps to 'I feel sick inside'

Stewart had little time to practice for the 500. On May 19, he had his best day of the month, setting what was then the highest average speed of that May at Indianapolis Motor Speedway, 226.683 mph. While his first day was promising for Stewart, troubles soon started to mount.

The next day, Stewart's 28th birthday, he made an uncharacteristic mistake and hit the wall going into Turn 3. "I feel sick inside right now because I know better and I'm a smarter driver than that,” he told IndyStar that day.

The car was undamaged, but because of Stewart's commitments in Charlotte, it was the last time he could drive it until Indy 500 qualifying. And at qualifying, there would be time for only one shot. Whatever speed he recorded would have to hold, Stewart got a bit of luck, drawing the second qualifying position out of the 44 drivers. Overnight rain had pushed the start back by an hour, which tightened up his schedule.

Qualifying at IMS, then racing                to Charlotte

Stewart began his Indy 500 qualifying run at 12:11 p.m. His four-lap average of 220.653 was more than six mph slower than his practice speed.

“There was rain, it wasn’t hot and humid,” Stewart said. “Qualifying had weather conditions that we weren’t able to be ready for.

“It was like running through water.”

He finished the Indianapolis portion of the day’s schedule in the 24th starting position, the outside of Row 8.

Stewart did one television interview then drove with a police escort to Indianapolis International Airport for his chartered flight to Charlotte. His flight departed at 12:50 p.m.

Stewart’s night in Charlotte proved to be more successful. He finished first in the Winston Open and finished second, behind Terry Labonte in The Winston.

Double-duty day

Stewart returned to Indianapolis for the 500, and ran an imperfect race. Benefiting from a caution inside his pit window, Stewart worked his way up to fifth by Lap 40, but he was never in contention to win the race.

His Indy 500 took a downturn when a pit stop during another caution took 30 seconds as the team made a wicker bill adjustment. The adjustment, which was intended to increase downforce on the back end of the car, slowed the car and Stewart ultimately dropped to 10th position.

Things got worse for Stewart when an out-of-window pit stop on Lap 139 went awry. Stewart left the stop early while the crew was making another adjustment to the wicker bill.

“We weren’t finished with the work that we wanted to do,” said Curry. Stewart said on the radio at the time that he left when the jack dropped the car. The whole ordeal caused Stewart to lose three laps and he eventually finished four laps behind.

Despite all that, Stewart finished ninth, his third-best finish in five Indy 500 races.

“It was fun out there — until we got a lap down,” he told IndyStar after the race.

But later that night in Charlotte, the stresses of the day caught up with Stewart. During the final 100 miles of the Coca-Cola 600 he felt sick from hunger. He was seeing things.

"The white line on the bottom of the track that's four or five inches wide went to two feet wide," Stewart told ESPN. "And a piece of hot dog wrapper would blow past and it looked like a pink-spotted elephant running across the back stretch."

Stewart toughed it out to to finish fourth. After climbing out of his car, Stewart's legs collapsed and he sank to the ground, AP reported. He sat with his head wrapped in a wet towel, drinking fluids.

Other drivers have tried, but Stewart remains the only driver to complete both races in a day.

Second try is even better

Stewart was so fatigued after his 1999 try that he vowed never to do it again. But he made his second and final double-duty attempt in 2001. He finished both races on the lead lap, to become the only driver to complete the full 1,100 miles with a sixth-place finish in Indy and third-place finish in Charlotte. This time, he'd have the help of a trainer hired from the Carolina Panthers, a requirement from Joe Gibbs.

“That was a game-changer,” Stewart said. “He was with me the entire three and a half weeks. He knew everything that went into my body. I felt great in the 500 and I felt good the entire 600, I finished Top Six in both of them so it was good enough to get the job done.”

He created widespread speculation in 2004 by making an unexpected visit to Indianapolis Motor Speedway on Bump Day. Stewart was seen in the Foyt garages and even put on a driver’s suit at one point. Nothing came of it, but the intrigue created a bigger stir than the on-track activity.

Five drivers have attempted the double. In 1994, John Andretti was the first to start both. Andretti started the Indy 500 in the third row, two rows behind cousin Michael and one behind uncle Mario. John ran as high as third and finished 10th, four laps behind winner Al Unser Jr. After flying to Charlotte, Andretti eventually finished 36th, dropping out on lap 220 with engine failure.

Davy Jones made an attempt in 1995 but failed to qualify in Charlotte. Robby Gordon made his first attempt in 1997 and qualified for both races, but the 500 was postponed by rain and was eventually completed two days later.

Talk still swirls from year-to-year about who will be the next driver to attempt the feat.

“I think Kyle Busch would do a good job,” Stewart said. “I know (Kyle) Larson would like the opportunity to do it. I think Busch is probably the one that would have the best opportunity. He’s got such a good feel for the race car. I know he’s expressed interest in doing it, so I would like to see him have an opportunity.”

Kyle's older brother Kurt Busch was the most recent driver to attempt the feat. Kyle was asked if he would like the opportunity to win an Indy 500 after winning the Brickyard in 2016. “There’s been some people out there that have expressed some interest,” he said. “So we’ll see where things kind of go.”

***

Today, Curry lives in Plainfield, Indiana, and maintains a close relationship with Stewart. He has been diagnosed with an advanced stage of Temporal Lobe Degeneration. Currently there is no cure and the prognosis is always fatal. Curry invites anyone wishing to help spread awareness to visit theaftd.org for more information.

Stewart retired from driving in NASCAR in 2016. He is co-owner of Stewart-Haas racing with Gene Haas. He holds ownership stakes in three tracks, including full ownership of Eldora Speedway in New Weston, Ohio.

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This article originally appeared on Indianapolis Star: Indy 500 history: Tony Stewart ran Indy 500 and Coca-Cola 600 same day