The winningest person in Indianapolis 500 history will be the celebrity pace car driver for next month's Indianapolis 500, IndyStar reported. Roger Penske never drove to victory lane at Indianapolis Motor Speedway. In fact, he never drove an Indy car there at all, deferring his chance to take a rookie test in 1964. Another hotshot eventually got that opportunity. Perhaps you've heard of Mario Andretti. But Penske went on to grow his automotive business into a global leader, and excel on the track he won races at a staggering rate. His record collection of Indianapolis 500 trophies stands at 16 - and likely counting. He has four drivers set for a chance at victory lane again this year, but this time he will literally and figuratively lead them there.