Indianapolis Monthly Magazine - Indianapolis Restaurants, Shopping, Concerts, Events and more. Class Photo: Legends of the Indy 500 - Dario Franchitti Starts: 8 Wins: 2 (2007, 2010) Claim to fame: A two-time Indy winner has to marry VERY well to end up with a spouse (stunner Ashley Judd) who overshadows him. And after a bumpy stretch in NASCAR, the Scottish hunk is back where he belongs.