#3 Jacques Villeneuve - 1995
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One year before beginning his Formula One campaign, 1997 F1 World Champion Jacques Villeneuve capped off his Indycar career with a world championship win in 1995, including an Indy 500 victory. Driving for Team Green, Villeneuve didn't have the best start to the race after getting a two-lap penalty for passing the pace car.
Nevertheless, the Canadian prodigy made his way to the front of the field and after a penalty befell then race leader Scott Goodyear, Villeneuve took the lead and secured an Indy 500 win. No doubt this made him an even more attractive prospect for Formula One teams in the coming year.
In 2014, Villeneuve made another Indy appearance, and while he didn't win, he did finish a respectable 14th at the age of 43.