Gotta be the first one, shared with my year-and-a-half-older brother. It was a 1947 Jaguar MkIV Drophead Coupe that had suffered an electrical fire, so we got it cheap, in 1961, with help from the 'rents. We started working on it before either of us were old enough to drive, and fixed it up in time for my brother to start driving it and me shortly thereafter. It was green, of course, right-hand drive, with a landau top and suicide doors. Huge chrome headlights and long sweeping fenders. A mechanical nightmare, of course, but it got me prepared for my later British cars (MGB Roadster, MGB-GT, TR-6, TR-7).
From a young male perspective in the 60s, I was blessed in the fun automotive arena: my dad was a car dealer and a collector. My brother and I were the slave labor for fixing up the cars he picked up here and there, from 1960 to 1969. As preteens we’d go to Summer School in the morning, and then go to dad’s dealership to work on whatever cars he had around to restore. Over the years these included a
[ul]
[li]1930 Packard 745 convertible coupe[/li][li]1933 Packard phaeton[/li][li]1929 Rolls Royce PII Springfield convertible sedan[/li][li]1935 Rolls Royce PIII Town Car[/li][li]1956 Lincoln Continental[/li][li]1960 Mercedes Benz 300SL (sorry, not a gullwing)[/li][li]1962 Ferrari 250GTE[/li][li]1940 Howard (sorry, this is an airplane. Mom was not amused at how long it was parked in the driveway.)[/li][li]Other, more short term, vehicles included a birdcage Maserati, 1948 Bentley, 1936 Packard, 1941 Packard, 1922 Chevrolet, 1934 Pierce-Arrow.[/li][li]Cars that showed up on the used car lot: XK120, XK140, XK150, XKE, 1965 Corvette w/396 porcupine head V8, 1962 Impala with 409 & 3-2s, bathtub Porshe, Hillman Minx, Mini-Cooper S, etc.[/li][/ul]
The summer I was working on the Ferrari I owned a Volkswagen Squareback named “Toby” (my starving student at UCSB days). I was able to take the Ferrari out on drives up Skyline Boulevard on the San Francisco peninsula and it was amusing to see how the “class lines” broke out. Corvettes averted their eyes, but Shelby 427 Cobras would essay a slight wave as we passed. The Ferrari was a joy to drive–no surprise, eh? With its V-12 and two four-barrel carburetors it would hunker down and scream when you put your foot down.
Remember the car waxing scene from “The Karate Kid”? Well, it took a full weekend to polish and wax the 1935 Rolls. It was a gorgeous black and chocolate brown paint job, and there were two acres of metal on this damn thing. Thirty-five years later I still can feel how sore I was.
But, Dad trusted my brother and me, regardless of our teen-ness, so we got to take the cars out. The most fun we would have with the '35 Rolls was for me to put on a dark suit, grab my great-grandfather’s lodge cap, and turn myself into a chauffeur. Then we would drag the main in San Jose, me in the separate chaufffeur’s compartment, and my brother waving Windsor-like from the back seat.
I mentioned that my dad was a car dealer. Back in the sixties things were a little looser. When we got rid of the Jaguar (whimper) my brother and I picked up a 1964 GTO convertible. We were able to get salesmen’s licences, so the insurance for each of us was $125/yr. That kept the family expenses down! The GTO, in impromptu drag races, humiliated the local Mopar and Ford fanatics, and years later ended up on the cover of Car and Driver (with an article that wasn’t quite the “Straight Dope.”)
But this was years ago. My most fun vehicle now is my Trek 5000 carbon fiber road bike. When my last car crapped out in March at 150,000 miles, I donated it to the towing company. Occasionally I will drive my wife’s Honda Del Sol, but most of my travel now happens on CalTrain or my bike.