Pyrroles, indoles, and carbazoles are among the most important families of nitrogen- containing heterocycles that occur frequently in natural products, pharmaceuticals, agrochemicals, and other functional molecules. Consequently, improved syntheses of these compounds con- tinue to interest synthetic chemists. This Focus Review describes recent advances in synthetic methods for producing these privileged heterocycles that feature transition-metal-catalyzed C-H activation approaches. Because of the common five-membered pyrrole core, some of the C-H activation approaches are applicable to two or more of the pyrrole, indole, and carbazole skele- tons. The reactions discussed here not only serve as atom- and step-economical alternatives to the existing synthetic methods, but also show the latest developments in organometallic chemistry and homogeneous catalysis.