The Corpus Paulinum can roughly be divided into four letter groups, the Thessalonian letters, the Hauptbriefe, the Prison Letters, and the Pastoral Letters. As New Testament style criticism has revealed, each of these letter groups displays a number of lexical, syntactical, and other stylistic peculiarities. In order to interpret this stylistic diversity in the Pauline corpus on a broader basis and to explore all possible explanations for the different stylistic phenomena, it proves helpful to take into account the scholarly explanations for similar style differences in the much larger oeuvre of Cicero. Cicero’s writings confirm the prevalent observation that the same ancient author could write in very different styles. In addition, they demonstrate how different communication situations, different text genres, and different addressees could influence not only Cicero’s but also Paul’s style.