2: 1964 Pontiac GTO Convertible
There was a time when the Pontiac brand was the focal point of the youth movement. The GTO was as much an automotive icon as the Mustang and the Chevelle. Designed by legendary automotive engineer John Delorean, the GTO was a massive success. Selling the thousands in its first year, the GTO broke almost every sales record imaginable (via Motorious).
Pontiac also got a nice bump in publicity when Car and Driver put the 1964 Pontiac GTO up against the Ferrari GTO and it won. Marketing in the 1960s was a lot different than it is today, and the GTO was a success in just about every way. Leno has taken pride in his GTO model and continues to be a Pontiac aficionado.