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.

The current-gen SL 63 is a 503-hp cruiser built on AMG's twin-turbo 4.0L V8, and it's competent at almost everything except justifying its $120k+ asking price against a 991.2 Carrera 4S. Mercedes prioritized opulence and tech over the raw engagement that made older SLs worth owning.