Jay hits the road to meet people who've had the courage to throw caution to the wind and go for it. He surprises country superstar Blake Shelton by taking him for a spin in a vintage pick-up truck with a "royal" connection. He goes head to head on the track with comedian turned professional racing car driver Adam Carolla in an endurance race. And Jay takes his life into his own hands when he agrees to teach Saturday Night Live legend Norm McDonald how to drive.