In the second half of the 20th century, especially during the 1960s and the 1980s, a growing number of cultural awards, particularly literary ones, marked the intellectual field ie literary art in Serbia. Among these, a special place belongs to the prizes established and given by social-political communities on federal, republic or local levels, which symbolizes the desire of the state and its parts to play the role of a modern benefactor. One of those prizes, which used to be rather prestigious over a long period of time, was the October Award of the City of Belgrade for contribution to art and science, but since 2008 it has lost its place in the culture awards nomenclature. This paper, thanks to participation of the author in the work of the jury of the October Award of the City of Belgrade for literature and translation in the period 1977-1980, reconstructs conditions under which the award was assigned, the authors and their works nominated, as well as the controversies arisen in some cases and reactions of the public. In this period, members of the jury have assessed 77 works, mostly writers’ pieces, a number of works by literary historians, theoreticians and critics, and much fewer translators. In two turns, the work of the jury was undoubtedly colored by the atmosphere of tolerance and concord in decisions on the winners, when a great role in this was played by the jury chairman, Vukoje Bulatović, the manager and chief editor of the “Politika” daily magazine at the time.