This chapter compares the illustration of Mary’s grief in Catholic and Protestant passion oratorios of the 18th century. The central question is in which way theological differences in the understanding of the mother of God—”co-redeemer” or “model believer”—are reflected in oratorio librettos and their settings in music. The discussion is primarily based on examples of oratorios in Vienna (H. Rademin/G. Reutter Jr.: Mater Dolorum; P. Metastasio/A. Caldara: La Passione) and Hamburg (C. F. Hunold/ R. Keiser: Der blutige und sterbende Jesus, J. U. v. König/R. Keiser: Thränen unter dem Creutze Jesu, J. U. v. König/G. Ph. Telemann: Die gekreuzigte Liebe). It can be observed that the illustration of Mary’s grief is, in Catholic as well as Protestant oratorios, not only determined by theological premises, but also by dramaturgical ones, especially in the settings to music of the librettos. This raises the question if the intensity or reluctance of pointing out Mary’s grief has to be interpreted as theological message or theatrical medium, if the theatrical concepts are created for theological purposes or can be seen as artistical independent expression. At this point, the chapter concludes that Mary’s grief in passion oratorios illustrates a deep amalgamation of religious education and musical entertainment. The character of this amalgamation does not depend on denomination background alone, but also reflects specific performance contexts such as church, court, or concert hall and the respective socio-cultural circumstances.