This critical review is dedicated to the anion complexation chemistry of amide- and urea-functionalized (benzo)pyrroles, such as pyrroles, indoles, carbazoles, isoindoles, naphthalenodipyrroles and benzodipyrroles. It provides a comprehensive overview of these simple and neutral anion sensors from the first examples up to very recent studies. There is a discussion of a gradual progress made over time, often based on careful analysis of the properties of former generations that have subsequently led to obtaining excellent effectivities and selectivities. The influence of these species on other fields of chemistry and their applications there are also discussed (57 references).