I selected the 250 GTO, but only because it's closest to my top picks: 250 GT Cabriolet Series I, 250 California Spyder LWB and 250 SWB Berlinetta.
Plus I noticed there weren't any pre-war cars on that list. In that case most of the Alfa-Romeo 2.9s and some of the Bugatti Type 57s would be on my list. And for the Americans car lovers any Duesenberg with a Murphy body.