2011, 12, or 13 S550
I think the W220 represents the last of the stately S Classes. There's a certain charm and elegance to the W220 that's not present in the 221. The 220 wants to pamper, coddle and insulate the occupants above all else. It's not a sporty car. While you could get an AMG appearance package and give the exterior a sporty pretense, the nature of the car didn't change.
I think that with the introduction of the Maybach handling the needs of the Grey Poupon crowd, Mercedes decided the 221 could lean more toward sportiness. The exhaust is louder, the ride is firmer, there's more road feel in the steering, the seats are more aggressively bolstered. In terms of a quiet, comfortable, serene driving experience, there is no direct upgrade to the W220.
Aesthetically, while the 221 is an attractive and more modern design, the 220 still holds up. I think an 04-06 S430 or S500 with the AMG package is a beautiful, timeless, classic design. I'm enjoying my S550 immensely and adjusting to the differences, but I do miss the 220s.



