10) Emerson Fittapaldi: Emerson Fittapaldi won the Indy 500 twice, in 1989 and 1993 for Team Penske. Fittapaldi’s presence goes far beyond the walls of the Brickyard, though. He was a fixture in Formula 1 in the 1970s as well, winning the world driver’s championship in 1972 and 1975, driving a Lotus and a McLaren, respectively. He remained in CART until 1996, having captured the series’ championship during the 1989 season.
9) Tommy Milton: Think winning Indy is tough? This guy did it twice. In the 20s. With one eye. Seriously, the guy was born with only one functioning eye, but still managed to win Indy during an era where death was downright common for racers, and in cars that required near-Herculean endurance to drive (not that today’s cars are much easier on drivers). His first win was behind the wheel of a racer built by Louis Chevrolet in 1921, while his second win came in 1923 driving a Miller 122.
8) Helio Castroneves: The only driver on this list still active, Helio Castroneves is one of the few back-to-back winners, taking victories in 2001 and 2002, along with his most recent win in 2009. Castroneves has been a fan favorite in recent years, due to his unique Spider-Man routine, in which he climbs the fence circling the track after each victory.
7) Bobby Unser: While not quite as successful as his brother, Al, Bobby Unser still managed to win the 500 three different times (1968, 1975, 1981). It was the last win, in 1981, that people talk about. Unser won the race, but the victory was given to Mario Andretti the following morning after Unser used the track apron to pass several cars under yellow, as he exited the pits. After a lengthy, five-month debate, Unser’s win was reinstated. The 1981 500 would be his last, as he skipped the 1982 race and retired from racing in 1983.
6) Johnny Rutherford: Another three-time winner (1974, 1976, and 1980), Johnny Rutherford was also the series champion in 1980, and wrangled wins at the other two 500-mile races in American open-wheel racing (Michigan and Pocono). He had limited success in NASCAR as well, winning one of the 100-mile Daytona qualifying races in 1963. Although it was his only Winston Cup win, it made him one of the youngest winners of a points-paying race at that time.
5) Wilbur Shaw: Shaw’s claim to Indy fame came from his three victories, including being the first driver to win the race two years in a row. He was the first to cover the 500 miles in 1937, 1939, and 1940. At the conclusion of World War II, Indy was in a bad way from years of disuse and neglect. Wilbur Shaw is credited with bringing Tony Hulman into the equation, and reviving the 500 in the post-war years.
4) Louis Meyer: Meyer was the first three-time winner of the Indianapolis 500, taking victory in 1928 (his rookie season), 1933, and 1936. After his win in 1936, he began the tradition of drinking milk after the race, and was one of the first drivers to win the pace car following his victory.
3) Rick Mears: Mears is the only other four-time winner of the race (and the most recent one to boot), with victories in 1979, 1984, 1988, and 1991. He’s also the current record-holder for poles at Indy, having started first in the historic race six separate times. He spent the overwhelming majority of his 17-year career at Team Penske, where he recorded all four of his Indy 500 wins, along with three championships.
2) Al Unser: Another four-time winner, Unser took the checkered flag in 1970 and 1971, leading over half the race in the latter victory and becoming one of the few to win the 500-mile race two years in a row. He also claimed victory in 1978, and again in 1987. His final win may have been the most remarkable, as a month prior, he was without a car or a sponsor. Roger Penske hired him to replace the concussed Danny Ongais. He won the race in a year-old March chassis, edging out Mario Andretti, who was suffering from mechanical issues, with fewer than two dozen laps left.
1) AJ Foyt: The first four-time winner of the Indy 500, AJ Foyt tasted milk for the first time in 1961, before winning again in 1964, 1967, and 1977. He wasn’t just an Indy master though, as he was dominating the USAC during the 60s. Foyt’s second win in 1964 was the last to be won by a front-engined racer.