The ride comfort of three Alfa Romeo cars, namely Giulietta (1955), Alfetta (1972) and 159 (2005) has been assessed both objectively and subjectively. The three cars belong to the same market segment. The aim is to let young engineers or graduate students understand how technology has evolved and eventually learn a lesson from the assessed trend. A number of cleats have been fixed at the ground and the three cars have traversed such uneven surface. The objective assessment of the ride comfort has been performed by means of accelerometers fixed at the seat rails, additionally a special dummy developed at Politecnico di Milano has been employed. The subjective assessment has been performed by a panel of passengers. The match between objective and subjective ratings is very good. Simple mathematical models have been employed to establish a (successful) comparison between experimental and computational results. The ride comfort differs substantially among the cars. The paper discusses the origin of the different ride comfort performances and provides a scientific understanding hopefully useful for future developments in the automotive engineering field.