The central theme of this review is the synthesis and subsequent study of a variety of π heterocycles with particular emphasis placed on the recognition of key steric and electronic factors controlling the development of heteroaromaticity as well as its less conventional variants, heterohomoaromaticity and heterobicycloaromaticity. The first three sections are devoted to the hetero[9]annulenes, their benzologues and the hetero[13]annulenes respectively and incorporate information attesting to the validity of Hückel's 4n + 2 rule in spite of frequent need for rather major, potentially damaging, skeletal readjustments. In each case, there is also unmistakable indication of an inverse relationship between heteroatom electronegativity and the development of 'aromatic' character. Section D contains information establishing the existence of bicycloconjugation in the 9-heterobicyclo[4.2.1]nona-2,4,7-triene system. Lastly, section E deals with the 2-heterobicyclo[3.2.1]octa-3,6-diene skeleton, incorporating data which are indicative of the system's ability to realize a homoconjugated frame.