Indiana native Tony Stewart has been a winner in every type of race car he's ever sat in: TQ midgets; USAC Silver Crown, sprints, and midgets; Indy Cars; and a number of NASCAR divisions. Even with an intense desire to win the Indianapolis 500, Stewart's competitive nature led him from the Indy Racing League to NASCAR's top ranks in 1999, and he has never looked back.
Stewart's 1999 Winston Cup campaign was the type of season many veteran drivers would love to have, but Stewart - in spite of many other race wins and championships - was still a rookie with Joe Gibbs Racing in the #20 Home Depot Pontiac. Two pole positions, 21 top ten finishes, and three wins led Stewart to a 4th place finish in the season-ending points standings, and he took the series Rookie of the Year award. In 2000, Stewart won six races, two poles, and took 6th in the final standings.
2001 saw Stewart finish 2nd to Jeff Gordon in the points standings, backed up by three wins. This is also the year Stewart became the first and only driver to date to complete "Double Duty" - he finished 6th at the Indianapolis 500, then flew to Charlotte, NC to compete in the Coca-Cola 600 at Lowe's Motor Speedway, where he finished 3rd - 1,100 miles races in one day.
Backed up by three wins, two poles, and 21 top ten finishes, Stewart took his first Winston Cup championship in 2002, holding off Mark Martin. 2003 was a bit of a disappointment, with Stewart finishing only 7th in points with two wins and a pole, but it was also a learning year, as Joe Gibbs Racing switched from Pontiac to Chevrolet.
2004 saw Stewart qualify 4th for the inaugural Chase for the Nextel Cup, falling back to 6th by the end of the ten-race series. A slow year for Stewart, he had only two wins. If 2004 was at all disappointing, he made up for it in 2005. He took his number-one seed for the Chase and never looked back, winning his second championship. He won five races, including the Allstate 400 at the Brickyard, his beloved Indianapolis Motor Speedway. After his second win of the season at the Pepsi 400 in Daytona, Stewart borrowed IRL driver Helio Castroneves' trademark celebration - climbing the front-stretch fence. This led to some classic advertising for Stewart's sponsor Home Depot - discounting ladders after his second "climb" in New Hampshire - the ads were captioned with "Hey Tony - we've got ladders" - and discounting bricks after his Indianapolis triumph.
2006 marked Stewart's most inconsistent year in Cup racing, missing the Chase by 16 points and finishing 11th in the final standings, in spite of five wins. Stewart suffered a shoulder injury after two accidents on Memorial Day weekend (Cup and Busch races), and drove in pain for many weeks after.
Stewart bounced back in 2007, with three wins and a 6th place showing in the Chase. He also won the season-opening Budweiser Shootout, a non-points race at Daytona. His three wins included his 30th career win at Chicagoland, and a second Allstate 400 at the Brickyard. 2008 was once again a slow year, with only one win and a 9th place Chase finish after Joe Gibbs Racing switched to Toyota.
In July of 2008, Stewart announced he had purchased half of Haas CNC Racing, and would rename it Stewart-Haas Racing for the 2009 season, leaving his ten-year association with Joe Gibbs, Home Depot, and the #20 to drive the #14 Chevy co-sponsored by Office Depot, Old Spice, and Burger King. Joining Stewart-Haas in addition to Stewart would be Ryan Newman in the U.S. Army #39.
Stewart's "bad boy" image is the result of a number of on- and off-track altercations with officials, other drivers, and the press alike. Over the years, he has had numerous entanglements with Jeff Gordon, Brian Vickers, Kyle Busch, Matt Kenseth, Clint Bowyer, and Kurt Busch, as well as photographers, reporters, and officials. Among his "highlights" were arguments with NASCAR over the mandated head-and-neck restraint, a pit road incident with Kurt Busch that nearly injured one of Stewart's crewmen, using profanity in his post-race interview after winning his second Brickyard, and ripping corporate sponsor Goodyear for poor quality tires.
He has, however, mostly used his NASCAR fame for beneficial purposes, founding the Tony Stewart Foundation in 2003. The Foundation raises funds for and donates funds to care for critically ill children, drivers injured in motor sports, and the protection of various animal species.