Back in the '80s I had a lot more "play" money, so chose some rather unusual "cages". Land-Rover Series 2A 109, Honda Z600, Bertone X1/9, VW Super Beetle. Then reality/practicality set in because I was car-pooling, resulting in an Audi 5000S and Audi 80 Quattro. When I stopped driving 100 miles a day, I started driving rusty old Mercedes diesels - first a '70 220D and for the last several years a '79 300CD.
I'm looking to replace the 300CD now and am leaning towards an Alfa Romeo (Milano or possibly 164) or Mercedes 190E. The former is quite unique, the latter not so much.
I'd like something a lot sportier, but with my mother increasingly depending on me for transportation to doctor's appointments and such, I need to stick with something she can get in and out of easily.