OK, I'll play. I started off with a '35 Ford with a warmed over 59A block and hydraulic brakes. Nice car for a 16 year old, but it wouldn't go to the beach without overheating, so I had to drive to where I had my Triumph hidden and ride it.
Next, I got a '41 Ford with a 59L block. That engine was the same as the 59A except that it was cast a bit thicker for use in wartime military busses. When you got one with the cores properly aligned during casting, you could bore it out 3/8, and I had one. Even with the big 2 core radiator that came in the '41 Super Deluxe, I couldn't make it to the beach in the summer.
Next was a '52 Plymouth. Not as glamourous or fast, but it handled very well for a large car and it never overheated. Eventually, a friend of mine got a '56 Ford with a 312 V8, so reliable alone wasn't enough anymore. I stuffed in a DeSoto Hemi set way back on the frame, and the Plymouth was unbeatable. It cornered even better too.
Then there was a string of soso cars, a '52 Packard 400, a '52 Olds Super 88, a '58 TR3 B+ (bigger bore than a TR4) and a '65 Chrysler 4 door with a 383 and lots of bells and whistles.
I liked the Chrysler enough that I got a '70 4 door with the 383 HP (330HP), 4 speed overdrive manual transmission, no A/C and no power anything. All 330 HP were for business use only.
Another dry spell followed by trading a 4.0 Jeep for a rather rare 383 powered Jensen Interceptor MK3. That was pretty quick. The OL got busted in it once doing over 140 out on the desert. So, she ended up with a 6 cylinder Volvo nd I ended up with a Dodge Ram 1500 with a 360.
Currently, we share an '06 Dodge Hemi Charger, a '51 Plymouth that is my next project and a '69 Dodge Utiline that is about to get a 400 V8/4 speed OD stuffed in it.
I also hope to win the lottery before the Challenger comes out, I really need one of those.