The effect of cyclopentafusion on the aromatic properties of pyrene and its cyclopentafused congeners has been studied by calculating resonance energies, using the valence bond (VB) method, and nucleus independent chemical shifts using DIGLO. The VB resonance energy is only slightly affected by cyclopentafusion. The resonance interactions between Kekule resonance structures that lead to six pi electron (benzene-like) conjugated circuits have the largest contributions to the resonance energy, in favor of Clar's model. For all compounds these contributions are of similar magnitude. Hence, according to the resonance criterion, all compounds have the same aromatic character. In contrast, the total NICS values show a decrease of aromatic character of the compounds in the series upon the addition of externally fused five-membered rings. However, in line with the resonance criterion, the diamagnetic part of the shielding tenser perpendicular to the molecular framework is nearly constant for all compounds, provided that comparable gauge origins are chosen. Thus, care should be taken by comparing the aromatic character of rings of different molecules by considering only their total NICS values.