In 1499, the Dutch-speaking poets Jan Smeken (†1517) and Johannes Pertcheval(† 1523) were among the founders of the Brussels chapter of the confraternity of the Seven Sorrows of the Virgin Mary. In this article, the role Smeken, Pertcheval, and other rhetoricians played in the onfraternity is explored on the basis of a hitherto unknown source, the accounts of the Brussels confraternity from 1499 to 1516. This privately owned document of almost 350 pages reveals among other things that Johannes Pertcheval enlisted thousands of names in the register of the confraternity (the so-called Liber authenticus, now in the Brussels City Archives) and that he was responsible for its decoration with several coats of arms. The article also focuses on the use of printed images and texts to promote the devotion of the Seven Sorrows and on a procession, which was organised annually by the confraternity from 1505 onwards. In the context of this procession, the rhetoricians staged a play enacting one of the Seven Sorrows of the Virgin every year from 1508 on, a cycle comparable to the seven Bliscappen also staged annually in Brussels. At least two of the now lost plays of the Seven Sorrows were composed by Jan Smeken, who received a reward equivalent to ten working days of a skilled craftsman for each play. More generally, the accounts shed new light on the dynamics in religious, artistic and literary life in Brussels.