Best classic look = W126 SEC, W124 AMG Hammer
W140 S600 looks different than regular S500. I can't pin down the difference, but it's apparent to me. And it looks beastly. And deceptively quick...kinda like a sumo wrestler wearing a fitted 3 piece suit.
Best sporty look = W201 190E 2.5-16v with the funky oversized spoiler and rolled fenders. I would kill to have that car as a daily driver. Failing that, the AMG hammer is a very close second.
Modern look = W211 facelift. The angular look makes it look very sharp. W212 facelift looks even better.
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