I drive a 1995 E420 and often times I feel like getting a newer car or even an older (more charming) mercedes.
The later model w210s catch my eye. Particularly the E430 V8s or E55s :-D or the E300 diesels. (Yes... diesels of V8s for me)
and supposedly those E430s are really reliable.
If you wanna keep it in the same 'class' I could only think of that car or the newest W211.
The W208 CLK is also a nice car. It's got a beefy stance and with a V8 it also sounds great. The interior doesn't look that nice though.
oh... What about a BMW E39? That is a nice looking car for sure. Not sure how reliable they are though. A late model 6-speed 540i with the Sport Package looks great inside and out
In fact, I'd take an E39 over a W210.