30 Days in May: No. 22, Tony Stewart, 1999 The Home Depot Dallara/Oldsmobile

Welcome to our monthlong countdown celebrating notable drivers and cars from the history of the Indianapolis 500!

Photo credit: Indianapolis Motor Speedway

Tony Stewart pulled double duty in 1999, notching top 10s in both the Indianapolis 500
and the 600-mile NASCAR race later that night.

30 Days in May: No. 22, Tony Stewart, 1999 The Home Depot Dallara/Oldsmobile. Tony Stewart was the first homegrown star of the Indy Racing League. His pedigree was perfect: An Indiana native who won USAC national titles in Midgets, Sprints and Silver Crown cars (all in the same season!) who proved immediately adept at driving Indy cars, too, winning races and a championship in those as well.

After running in the IRL from 1996 to 1998, Stewart became a full-time NASCAR driver, appearing in the 500 just two more times (1999 and 2001). Stewart was fast right off the bat in stock cars, too, and finished his NASCAR career with three Cup titles and two wins in the Brickyard 400.

In the 1999 Indianapolis 500, Stewart finished ninth, four laps down to winner Kenny Brack. But Stewart’s workday was just beginning, because he flew from Indianapolis to Charlotte, North Carolina, to compete in the 600-mile NASCAR race that night and finished an impressive fourth.