High-speed railway bridges are subjected to normative limitations concerning maximum permissible deck accelerations. For the design of these structures, the European norm EN 1991-2 introduces the high-speed load model (HSLM)—a set of point loads intended to include the effects of existing high-speed trains. Yet, the evolution of current trains and the recent development of new load models motivate a discussion regarding the limits of validity of the HSLM. For this study, a large number of randomly generated load models of articulated, conventional, and regular trains are tested and compared with the envelope of HSLM effects. For each type of train, two sets of 100,000 load models are considered: one abiding by the limits of the EN 1991-2 and another considering wider limits. This comparison is achieved using both a bridge-independent metric (train signatures) and dynamic analyses on a case study bridge (the Canelas bridge of the Portuguese Railway Network). For the latter, a methodology to decrease the computational cost of moving loads analysis is introduced. Results show that some theoretical load models constructed within the stipulated limits of the norm can lead to effects not covered by the HSLM. This is especially noted in conventional trains, where there is a relation with larger distances between centres of adjacent vehicle bogies.