In the past two decades, transition metal-catalyzed C–H functionalization followed by annulations with various coupling partners has received much attention in organic synthesis. In particular, Rh(III) or Ir(III) catalyzed regioselective C–H functionalization followed by the cyclization of diverse arenes with metal carbene precursors has become a highly investigated research field in recent years. The purpose of this review is to provide a comprehensive essay on the Rh(III)/Ir(III) catalyzed C–H functionalizations/annulations via carbene migratory insertion, focusing on the diverse metal carbene precursors with arenes/alkenes reported so far. The highlighted examples are categorized by nitrogen, oxygen, sulfur-containing heterocycles and carbocyclizations. Further, key mechanistic approaches are also briefly described.