Born in Columbus, Indiana, Stewart grew up racing go karts, and he raced them highly successfully, winning the world karting champion in 1987. He raced three-quarter midgets for a handful of years before moving up to the USAC series. Stewart was the USAC rookie of the year in 1991, and was the National Midget series champion in 1994.
In 1995, Stewart became the first driver ever in USAC history to win USAC's version of the Triple Crown, earning championships in all three of USAC's major divisions, National Midget, Sprint, and Silver Crown, in the same year.
Stewart graduated to the Indy Racing League for it's inaugural season in 1996, driving for Team Menard. He was second in the series' first ever race in Orlando. Stewart started on pole for that year's Indianapolis 500 after the original pole-sitter, teammate Scott Brayton, was killed in a practice crash. Tony led 44 laps of the race but had a blown engine end his day at lap 82. At the end of the season (which consisted of just three races), Stewart was 8th in ponts and was the series' rookie of the year.
When he wasn't racing Indy Cars, he raced stock cars. Tony also made a handful of starts in NASCAR's Busch Series that year. In 9 races, however, he had only a best finish of 16th place. He had more success in a one-time drive in the Craftsman Truck Series, where he finished 10th.
Tony was poised to improve his IRL standing in 1997, but struggled with finishing at times. He failured to finish the first three races of a ten race schedule, but recovered to finish second in Phoenix. At the year's Indy 500, Stewart had a good enough car to win his first IRL race, as he led 64 laps, but tailed off near the end of the race and settled for 5th. Tony finally got his first career win at Pikes Peak, as he led all but 7 laps of a 200 lap race. He became the leading contender for the series' championship after a bad slump by points leader Davey Hamilton knocked him out of first place. Despite an average end to his season, finishing 7th, 14th, and 11th, and 5 failures to finish overall, Stewart did just enough to beat Hamilton for the IRL title.
As he had done the previous year, he raced a handful of Busch Series races. This time, he was racing for Joe Gibbs, the former coach of the Washington Redskins who was having a lot of success with driver Bobby Labonte in Winston Cup. When Stewart was able to finish, he was in the top 10, and had a 3rd place in Charlotte. Stewart so impressed Gibbs that he was signed to drive the majority of the Busch schedule in 1998 to go along with a full-time IRL schedule.
The double duty did not effect his peformance in either series. In the IRL, he would win twice and finished 3rd in the championship. Stewart might've considered the season as something of a disappointment, as he finished dead last at the Indy 500 because of an engine failure.
On the Busch side, he finished in the top 5 five times in 22 starts. He came extremely close to winning his first Busch Series race in Rockingham, but was beaten on a last lap pass by Matt Kenseth. Stewart finished a solid 22nd place in 22 (of 31) starts, ahead of 6 drivers with more starts, and had an average finish that was comparable to some of the series' top 10 finishers. Gibbs had enough confidence in Tony that he was moved into Cup for the 1999 season. With his move to Cup, Stewart ended his 3 year career as a full time IRL driver.
Stewart started his Winston Cup career with a bang, as he qualified his #20 Home Depot Pontiac in second place in his first Cup race, the Daytona 500. He also showed a lot of fearlessness in one of the Gatorade Twin 125 races, as he was involved in a great battle with Dale Earnhardt for the win. The Intimidator came out on top, but Tony had nonetheless impressed quite a few people with his performance. In the 500 itself, Stewart ran near the front until problems with the car relegated him to a midpack finish.
Stewart spent most of his rookie season wowing people, as his car was often in the top 10. He only failed to finish a race once, and even then he finished 9th. He won a pair of pole positions at short tracks, and tied a rookie record with 3 victories. He finished his first year an incredible 4th in points, the highest points finish by a rookie in the modern era (since 1972), and only bested by James Hylton, who finished 2nd as a first-timer in 1966. Not surprisingly, he ran away with the Winston Cup Rookie of the Year award.
Tony also attempted to race 1,100 miles on Memorial Day, as he attempted to race the Indy 500 during the day and the Coca-Cola 600 in Charlotte at night. His attempt at "The Double" was mildly successful, as he finished in the top 10 at both races, but he fell 10 miles short of completing all of the miles.
Stewart showed no signs of a sophomore slump in Winston Cup in 2000, as he won 6 races. However, he "slipped" to 6th place in the standings because of a handful of DNF's, and an increase in the number of competitive drivers, among them his teammate Labonte, who won the Cup championship. Tony also began to get some bad press for his on-track incidents. The most well known of these came at Watkins Glen, when he and Jeff Gordon tangled and crashed into each other. Stewart made his displeasure towards Gordon known in an obscenity-laden tirade. The two are still heated rivals to this day.
Tony's 2001 got off to a frightening start, as he was involved in a nasty crash in the Daytona 500 where his car violently flipped over several times. Amazingly, he was mostly unhurt. He recovered to win 3 more races, and as he'd done before, ran near the front most of the season. Statistically, he had a worse season than 2000, but he was the runner up to Jeff Gordon for the Cup championship.
The season was not without controversy though. Gordon pulled a "bump and run" on Stewart to win a race in Bristol, and it resulted in Tony Stewart retailating in a post-race incident. Stewart was fined and placed on probation by NASCAR. He got into further trouble at Daytona, when he confronted a Winston Cup official after ignoring a black flag. At the same race, he also got into an incident with a reporter, kicking away a tape recorder. This resulted in another fined and longer probation.
He confronted the same official during a race in Talladega after refusing to wear a mandated head and neck restraint. Stewart was not allowed to practice until wearing one, and only managed to practice after his crew chief intervened. Tony, understandably, earned a reputation for being NASCAR's bad boy.
A more positive highlight of his 2001 season was a second attempt at The Double. This time, he succeeded in racing all 1,100 miles, finishing 6th at Indianapolis and 3rd in Charlotte. It is, to date, Stewart's last attempt to race both races.
Tony started his 2002 even more inauspiciously than he'd started his previous season, as his Daytona 500 lasted just 2 laps due to a blown engine. He won twice early in the season though, but was only 7th at the halfway point of the season. The second half of his season was plagued by an altercation he had with a photographer after the Brickyard 400. The incident put Stewart on probation by NASCAR for the rest of the season. Stewart went on to win the race immediately after he was disciplined by NASCAR, and went on a terror in the final races, finishing consistently in the top 5. At the end of the year, Stewart held off a charging Mark Martin to win his first Winston Cup championship.
As the defending Cup champion, Stewart managed to have a relatively incident free 2003. Now driving a Chevrolet instead of his usual Pontiac, Tony actually had his worst Cup season, but it was still good enough for a 7th place finish in points. He only won twice that season, but led more laps than he'd done the previous year and was highly competitive in the final races of the year.
In addition to his Winston Cup gig, Stewart, nicknamed "The Rushville Rocket" (for his present hometown of Rushville, Indiana) and "Smoke", is also the owner of a World of Outlaws sprint car driven by Danny "The Dude" Lasoski. He also still makes the occasional cameo on dirt tracks, appearing regularly at an ARCA race on dirt and at two prominent sprint car events, USAC's Turkey Day Shootout, and the indoor Chili Bowl Midget Nationals. Stewart will also make an apperance driving the 24 Hours of Daytona in 2004.