Imidazoles and benzimidazoles are quite unique and universal scaffolds, which are core units in numerous drugs and drug candidates. Exhibiting unique properties, they can be viewed as amide-bond and indole bioisosters, but offering additional options for interactions. After a more general description of their intrinsic physicochemical and structural properties, the most important, as well as instructive examples of marketed drugs utilizing imidazoles and benzimidazoles as scaffolds will be presented and briefly discussed.