I wish I could say I came up with this all by myself, but I read a Jalopnik article of the same title and it got me thinking. And then I figured you guys would have some cool answers too.
So, for my parents. Well, my mother didn't get her license until well after my parents were married and usually just drove some regular commuter car that my father bought. But my father, well, he had some cool stuff. Nothing like a Ram Air IV GTO Judge or a Hemi Car or a Porsche, but still cool.
His first car, which he still owns, was a '67 Ford Galaxie 500 convertible. Blue, with a black top and dark blue interior. Someone had yanked the 289 it came with and put in a 390 at some point, as well as adding the 390 badges. He saw it every day on the school bus on his way to high school and one day it had a For Sale sign and he took out a loan and bought it and drove it for years. It's relatively intact and rust free, but I guess it has some old collision damage lurking and the Ford fullsizes also had frame troubles. He has a lot of the stuff to restore it, other than time. Photo isn't his, but similar.
He also had a Jeep CJ5 with the 258 and a 4-speed that he bought cheap from an impound auction, repaired it and then drove it all the time. He loved that rig, and talks about getting it airborne off of sand dunes and driving it through the winter and how it would go anywhere. Rust eventually claimed it. It sat out behind the shed with a tree growing through it when I was a kid. He still wants another but the CJ5 market is insane.
Arguably the coolest though, and his only real hot rod, was he bought a '77 Buick Regal 2-door, light metallic blue, with a white Landau top and interior. Then he ripped out the running Buick 350 V8 and installed a 1969 high-compression Oldsmobile 455 and a TH400. Just because. It had something like 2.74:1 gears, and with the Q-Jet would get pretty good mpg, while still being reasonably quick thanks to Oldsmobile bulldozer torque. He remembers getting nearly 20mpg going down to PA. He still talks about the time that he did a burnout with it, and the rear gears generated so much wheel speed he jokes that he thought that the tires wer going to rip off the rims. It did leave divots in the pavement. No clue what happened to that car, but the Olds 455 and TH400 is still in the back shed, which I nearly installed in an '85 LeSabre Limited Estate.
Again, not the exact car, but very similar.