This feature article covers new directions in the fundamental and applied chemistry of the closo-carborane anions [HCB11H11]- and [HCB9H9]-, as well as some related chemistry with the dicarbolide ion [H2C2B9]2-. Specifically the manuscript will focus on summarizing the authors' as well as related novel contributions to the field. The application of such clusters as solution based electolytes for Mg batteries and related materials for ionic liquids will be discussed. In addition, the preparation of heterocycles and radicals fused to carborane anions will be discussed as well as various novel chemical transformations. Furthermore, new developments in anionic carboranyl phosphines and N-heterocyclic carbenes in the context of catalysis will be summarized.