My dad is a car guy, but he's also a guy who didn't have a lot of spare time or money when we were kids. My parents' first car with air conditioning was a 1995 Ford Explorer (their first new car since 1979). I was a junior in college when they bought it.
My first car as a kid was a '71 or '72 VW Microbus. I remember (as a five year old) shopping for our brand new 1979 Microbus. It had a 2.0 liter, air cooled engine, and it struggled getting up hills in the Sierra (not as much as the older one did, though). Right around that time (just after) both the Chrysler minivan and the Jeep Cherokee got very popular. Of course, ten years later, the SUV began taking over. My dad bought a 1950 GMC 150 (3/4 ton) pickup in the early 80s. That was the car I learned to drive on. You started it in 2nd gear because 1st was too low for any practical application on roads. 228 straight six, I think. Max speed: 56 MPH, and that was with a lot of lead time. Brakes and steering were horrible. Had to use a starter pedal to get her running. The cab had a rust hole on the passenger side, so you could watch the road go by. It still does, and you still can. Dad put seat belts in sometime in the late 80s. He upgraded to a 12V system about 15 years ago, and I think he had the brakes upgraded, too. As he nears his retirement (should have retired a while back, but he loves his job), he wants to finally really restore it, but most body shops want nothing to do with the cab. The engine serial number matches the frame, so it has that going for it as restorations go.
Right around when I was learning to drive, my grandfather gave my parents his 1973 Dodge Dart 2-door Swinger. When he bought it, they were only available in automatic, which--to him--was impractical, so he had a three speed manual installed, with a Hurst floor shifter. With the 225 slant six it wasn't speedy, but it had decent torque in the 40-60 range, and it was fun to slam the shifter around. Max speed somewhere around 105 (I had it there once, briefly, on an interstate, and in that car it terrified me, so it didn't last long, and that was as a teenager! I had an Acura up over 115 once around the same time and relatively speaking, it was smooth as glass). It had lap belts in front, and a shoulder strap you could connect (and should) from above the doors.
The Dart developed some cooling issues, and during one summer whenever I drove it to Sacramento, I would have to nurse it at about 55-60 MPG with the heater on full blast to keep the thing cool enough. Not a great way to drive in the Sacramento valley in the summer time, but normally when I was headed out there it was at night, so at least a little cooler. Pretty sure that turned out to be a blown head gasket. Dad and I also went to check out another GMC down near Bakersfield to see if it was worth buying and we blew a radiator hose south of King City (which is kind of the middle of almost nowhere). With no auto shops open Sunday morning, we duct taped that sucker, and it got us where we needed to go. The Dart and the Jimmy were great cars to learn on, among other things because they were so easy to work on, and thus understand how cars work.
Mom and dad were going to give me the Dodge when I graduated college, and my buddy and I were thinking seriously about how we would get a 318 V8 into it. Alas, the week before I graduated, mom was in a wreck and the car was totaled (she was ok, though pretty shaken up). Instead, I bought a 1990 Honda Accord 4-door, which was a much better car, but no where near as much fun (it did have AC, though).
My favorite car (that I've owned) to date was my Honda Odyssey (2006). Owned it for 13 years. Did its job remarkably well. Not at all cool, but I've moved on to wanting my car to do its job and nothing really more than that. And my personal leanings being what they are, the gas mileage is important to me. For a while I thought our replacement would be a Toyota 4-Runner, but in the end logic won out and we have an Accord Hybrid--another great car. Whenever we need a 4WD vehicle, we rent one (about once or twice a year). That works great, and saves us all kinds of money.