This low-mileage W222 S560 represents the last generation before Mercedes decided to make everything a tablet on wheels. The twin-turbo 4.0L V8 makes 463 hp through a nine-speed auto to all four corners, finished in Selenite Gray over black Nappa—the kind of spec that ages better than the infotainment systems that ship with these things. Values on clean examples have stabilized, making now the moment to buy if you've been watching.

This W463-generation G320 spent time in Japan before stateside import, arriving with black-on-black aesthetics and the original 3.2L V6 paired to a five-speed automatic. It's the kind of G-Wagen that proves the model's ageless appeal—twenty-six years old and still commanding attention, especially as import G's tick up in value.