Just thought of a few more after seeing them on the road.
Land Rover Discovery - Series III to IV
While the Series I and II are still the best looking Disco's, the Series III at least kept the original design and modernized it a bit, making it even boxier and keeping all the touches such as the unique roof and window design, still differentiating it from other LR's of the time. The Series IV however took things too far in making it modern. While not bad looking from the front or sides, the rear is an automotive equivalent of a stroke with the license plate design. It looks more like every other LR than a Disco in my opinion and lost all of its rugged looks. Honestly the new Defender should have been called a Disco Sport.
Audi A4 - B5 to B6
Despite the designs being overall very similar the B5 just looks much better and lighter as a result and honestly a bit more athletic in its looks with its slim and sharper design. The B6 isn't an ugly car, but the pedestrian models were very cheap looking and the rear end was not my favorite looking.
Mercedes-Benz E-Class - W124 to W210
The W124 is just a superior car in many aspects, but especially looks. Clean, timeless, and sharp, its just beautiful whether Sedan, Coupe, Cabriolet or Touring. The W210 on the other hand is very controversial, curvy, soft, and double headlights made it look heavier and less sharp, while not helping it age well. The Touring model especially was ugly. AMG variants helped (as shown) but most regular models were not as good looking. The W211 really fixed this design, showing how despite its controversial elements it could transform into something much better looking.
