Wow! I've owned twice as many cars as Uncle Ken but I haven't had one in nearly forty years. All were used (very used), and ranged in price from fifty to three hundred dollars. Those were the days when a dollar seemed to go a lot further, and gas was cheap.
The first car, bought when I was 17, was a '56 Imperial (2 door hardtop) for the whopping sum of fifty bucks. That thing was huge, but it had power seats, power windows, the dandy 3 speed (buttons!) TorqueFlight transmission, and a very thirsty 354 Hemi with dual exhausts. Mileage was terrible: 8 in the city and maybe 13 on the highway but teenagers don't care about such trivialities. The huge interior space was just the thing for a young pup on the make, and it was amazingly quick.
The second car was a '60 Falcon Ranchero, and I think I paid $150. I bought it when I returned from overseas, on my way to Ft. Rucker in Alabama. It was red with a white top, but I grabbed a bunch of cans of spray paint and painted it camouflage, with flat black bumpers and a flat black racing stripe on the hood. Way ahead of it's time, I like to think, and it went over very well down South despite the Land of Lincoln license plates (which I switched to Alabama plates, toot sweet). To further hide in plain sight amongst all the rednecks, I cobbled a fake gun rack out of cardboard, painted to look like wood. It worked; nobody was the wiser and I got some compliments.
Car number three was a '60 VW Microbus, and I think it was $300 (I forget, might have been only $150). Mr. Beagles is right, those heaters on VWs were terrible in the Beetles and worse in the Microbus. The hot (!) setuup was to get the optional gas heater which was available as an option. My bus didn't have one, and it got damn cold in the winter. Sometimes the windshield wipers didn't work, but that was okay because you could manually move the wipers from the driver's seat. Dog slow, with a top speed of maybe 60 (downhill) but snappy off the line for thirty feet or so. It was geared so low that regardless of the payload the acceleration (if you want to call it that) and top speed didn't change much. Blew the engine, but the replacement was very easy. Only 4 bolts to undo, and it took me about an hour, working alone.
The final car was the pricey one, the $300 '67 Fairlane 2 door, another hardtop. Nice 289, with a big Holley carb, Hooker headers, Thrush pipes, and the 3 speed Cruis-O-Matic. Mileage was only fair, but it sounded great.
Except for the Ranchero, all those cars had terrible rust problems, which was typical for that period. After three years most cars seem to start to rust through, unless you spent the dough for Ziebart rustproofing and even that didn't work all the time. You didn't see any ten year-old rust free cars in those days, unless they were from Arizona or some dry place like that. They don't call it "The Rust Belt" for nothing.
Okay, modern cars all look like lozenges and I can seldom tell the difference between them, although Mustangs still look like Mustangs. But the improvements are astounding, I think. They are all eerily quiet at highway speeds, none of that wind noise that I recall from my days of youthful indiscretion. Gas mileage and safety features are so much better that it's ridiculous, and everybody has power windows, air conditioning, and good sound systems. No cheesey AM radios with a tiny speaker in the steel dashboard. They seem expensive to me, but that just might be because of inflation.
I don't know if the new cars are fun to drive. They don't seem to be too easy to "work on" like the old ones, but they are much more reliable according to most reports I've read. Not much goes wrong. But I still miss, for different reasons, those old beasts of my misspent youth.
There are still some cars I wish I owned, if even for a short time. The '53 Studebaker Starlite coupe, designed by Raymond Loewy; the'63 Pontiac Grand Prix 2+2 with the Kelsey-Hayes 8 bolt wheels (dark blue!); and a '65 Dodge Coronet with the 426 Hemi. No automatic transmissions, please. Fun cars all, and I bet that Jay Leno has one of each in his garage.
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