1956 Ford Fairlane, my first car.  Unfortunately, it had problems I couldn't afford to fix, so I didn't have it long.

My second car, and the first one I bought with my own money-- a 1966 Pontiac Bonneville convertible.  What a wonderful automobile.  I am not a car person, and take great delight in thinking that I will never have to own another car in my life.  But...if I could own this thing again (and if I could afford the enormous gas bills), I would reconsider.