Known as "the greatest preacher in the early church", John's sermons have been one of his greatest lasting legacies. Chrysostom's extant homiletical works are vast, including many hundreds of exegetical sermons on both the New Testament (especially the works of Saint Paul) and the Old Testament (particularly on Genesis). Among his extant exegetical works are sixty-seven homilies on Genesis, fifty-nine on the Psalms, ninety on the Gospel of Matthew, eighty-eight on the Gospel of John, and fifty-five on the Acts of the Apostles.
The sermons were written down by the audience and subsequently circulated, revealing a style that tended to be direct and greatly personal, but was also formed by the rhetorical conventions of his time and place. In general, his homiletical theology displays much characteristic of the Antiochian school (i.e., somewhat more literal in interpreting Biblical events), but he also uses a good deal of the allegorical interpretation more associated with the Alexandrian school.
John's social and religious world was formed by the continuing and pervasive presence of paganism in the life of the city. One of his regular topics was the paganism in the culture of Constantinople, and in his sermons he thunders against popular pagan amusements: the theatre, horseraces, and the revelry surrounding holidays. In particular, he criticized Christians for taking part in such activities:
John's homilies on Saint Paul's Epistles proceed linearly, methodically treating the texts verse by verse, often going into great detail. He shows a concern to be understood by laypeople, sometimes offering colorful analogies and practical examples. At other times, he offers extended comments clearly intended to address the theological subtleties of a heretical misreading, or to demonstrate the presence of a deeper theme.
One of the recurring features of John's sermons is his emphasis on care for the needy. Echoing themes found in the Gospel of Matthew, he calls upon the rich to lay aside materialism in favor of helping the poor, often employing all of his rhetorical skills to shame wealthy people to abandon conspicuous consumption:
Outside of his sermons, a number of John's other treatises have had a lasting influence. One such work is John's early treatise Against Those Who Oppose the Monastic Life, written while he was a deacon (sometime before 386), which was directed to parents, pagan as well as Christian, whose sons were contemplating a monastic vocation. The book is a sharp attack on the values of Antiochene upper-class urban society written by someone who was a member of that class. Chrysostom also writes that, already in his day, it was customary for Antiochenes to send their sons to be educated by monks. Other important treatises written by John include On the Priesthood (one of his earlier works), Instructions to Catechumens, and On the Incomprehensibility of the Divine Nature. In addition, he wrote a series of letters to the deaconess Olympias, of which seventeen are extant.
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