Big old cars are fascinating because they really show what driving is about. In both mechanical terms and overall design. A lot of post 1960 cars have boring yet functional designs. Where are the times that cars had a posh dashboard rather than recycled plastic? Where are the times that adding ornaments, additional fenderlines and so on in favour of a better looking car was normal? As for the mechanical improvements it's good to have power steering and power brakes for easy and safe driving but it removes the feeling of driving a big and heavy car. Driving an oldtimer without power-everything is a pure form of driving; you, the car and the road.
So where are those times? They are today! This is where my interest for old cars kicks in and I'm lucky to have access to various old cars because my parents own a Mercedes Ponton 220S (1956) and Mercedes 280CE (1979). In the family two uncles are into old cars (Mercedes and Bentley) so I've seen various old cars.
Mainly two types of American 50'ies cars exist: from 1949 to 1953 and from 1953 to 1959. The latter are the rocket-style cars with tailfins, the first are "new generation" cars with just a big front grille. The grille in the previous cars (1948 and earlier) is big too but the overall style of the car is a tad different. My interest goes to the first "new generation" Pontiac from end of 1949, Pontiac Star Chief 1958 and Buick Roadmaster 1958.
In mechanical terms and design I like the Pontiac 1949 most. The Pontiac sports an old-style flathead engine and it's design is at least to say 'gorgeous'. When I saw this Pontiac I knew I wanted one. Since then I've actively looked around for a Pontiac and eventually found one.