There's no easy answer to the titular question, but the 3.2-liter Porsches from the mid-eighties are worth giving some serious consideration. Perhaps it's their unmistakable rasp, or those pedals mounted from the floor, but there's something exciting about this generation of the 911. Barring the turbocharged models, these simplistic 911s weren't known for outrageous levels of power, but a 2,700-pound curb weight and the analog steering endeared them to legions of fans.
Some of this model's distinguishing traits have been identified and appreciated by an up-and-coming YouTuber, though he doesn't admire the idiosyncrasies of the notchy 915 gearbox. The driver involvement, the petite proportions, and the responsiveness of the analog package are more than enough to make a young man—likely raised on Xbox—wax lyrical. That show of emotion and appreciation of quality mechanics makes me feel there might be hope for an amicable future between my tech-addled generation and classic cars. Godspeed, Mr. Checkpoint.