We analyze the relationship among the molecular structure, morphology, percolation network, and charge carrier mobility in four organic crystals: rubrene, indolo[2,3-b]carbazole with CH3 side chains, and benzo[1,2-b:4,5-b′]bis[b]benzothiophene derivatives with and without C4H9 side chains. Morphologies are generated using an all-atom force field, while charge dynamics is simulated within the framework of high-temperature nonadiabatic Marcus theory or using semiclassical dynamics. We conclude that, on the length scales reachable by molecular dynamics simulations, the charge transport in bulk molecular crystals is mostly limited by the dynamic disorder, while in self-assembled monolayers the static disorder, which is due to the slow motion of the side chains, enhances charge localization and influences the transport dynamics. We find that the presence of disorder can either reduce or increase charge carrier mobility, depending on the dimensionality of the charge percolation network. The advantages of charge transporting materials with two- or three-dimensional networks are clearly shown.