The ugliest car I bought and drove Had to be the 1962 Plymouth Wagon I bought back around 77 from my boss for $250 bucks. It was good runner, I even made a trip to Tahoe in it after driving it for most of a year. The trip was it's last, as I changed the oil using a good detergent oil, and it had never had detergent oil in it, so it loosened up all the old deposits and plugged up the oil passages, and started knocking on the way home. Here is a picture of one, mine was a faded blue.
The best car I ever owned till maybe 3 weeks ago was the 67 Olds 442. What I mean by 3 weeks ago is I just bought a Jeep patriot. Mine was a dark Metal flake Blue. I wish I still had that car! Here are a few pics I found online.
I could bring both front wheels off of the ground with car, it had a nice Dana 411 gears with a semi posi rearend. I usually only got one wheel off of the ground though. I never drove it as hard as I could have.