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This paper explores Cicero’s experimentation with satire, a genre with which Cicero is not generally associated, within another genre in which he is a central figure, namely, Roman prose letters. This paper will argue that Cicero’s introduction of satire into his familiar correspondence is not superficial or casual. Rather, it suggests that Cicero turned to satire for the relief it afforded him at a period when his freedom of speech and action was otherwise exceptionally constrained by the ascendancy of Caesar. The necessity for Horace of renegotiating the freedom of speech enjoyed by Lucilius is a familiar theme in scholarship on the Sermones. But the challenge of speaking in a regime that curtailed frank expression was not new in the Augustan era. Cicero’s letters to Atticus and other close correspondents during Caesar’s regime are rife with his dissatisfaction at restrictions on action and speech (e.g. Att. 12.4, 13.31; Fam. 9.6.2, 9.16.3). But whereas his tone in letters to some addressees is somber, his letters to Papirius Paetus are remarkable for their playfulness. Scholarship on the letters to Paetus has often focused on their humor, and particularly how Cicero ribs his Epicurean addressee with bulletins about his own forays into hedonism (e.g. Griffin 1995, Hutchinson 1998, Leach 1999, Morello 2013). Cicero’s care in matching tone and topics to the interests and temperaments of his addressees is an extremely attractive facet of his letters, and a measure of his skill as letter-writer. However, in the jocularity of his letters to Paetus (Fam. 9.15-26) we see Cicero merge the charming wit of a master epistolographer with the aggressive pose of a satirist. Hutchinson sees the “comic projection of a confident and threatening persona,” in Fam. 9.20, whose joking tone gives way in the letter’s conclusion to “shameless and pitiless aggression” (1998, 197). Hutchinson compares this persona to Terence’s parasite Phormio, but it is also possible that Cicero has satirical poses in mind. In the first letter of the series, Cicero congratulates Paetus on his old-fashioned wit (accedunt…Romani veteres atque urbani sales, 9.15.2). Paetus recalls the great Roman wits of old (Itaque te cum video, omnis mihi Granios, omnis Lucilios,…Crassos quoque et Laelios videre videor, 9.15.2). In another letter he declares that he too has plenty of “salt” (salis enim satis est, 9.16.10). We might compare Horace’s praise for Lucilius (quod sale multo/urbem defricuit, Satire 1.10.4-5). But the most direct indication that Cicero had Lucilian satire on his mind in this period occurs in a letter to Atticus reporting on a visit from Caesar in December of 45, in which Cicero directly quotes Lucilius. The meal with Caesar was surprisingly successful: bene cocto et/condito, sermone bono et, si quaeris, libenter (Att. 13.52.1 = Marx 1122). The same line occurs at De Finibus 2.25, where Cicero places it third in a series of Lucilian quotes on the philosophically unsound gourmandizing of Gallonius in contrast to the plain food preferred by Laelius. Of twelve letters to Paetus, half deal with dining. In the letter written last in the series, Cicero laments the news that Paetus has given up dinner parties. He urges Paetus to resume his old mode of conviviality not for the food, but for the conversation (nec ad voluptatem refero sed ad communitatem vitae…quae maxime sermone efficiter familiari, Fam. 9.24.3).Whether or not Cicero the satirist emerges fully from this correspondence, the letters to Paetus certainly show Cicero to be far less constrained by generic boundaries than modern interpreters of his work often have been. Moreover, we may observe that even in a weakly bounded genre like the familiar letter, allusion to other genres can be deployed to subtly underline a point. In this case, Cicero’s satirical riffing in the letters to Paetus stresses the difference between his own time and that of Lucilius. The freedom to criticize one’s eminent dinner partners that flourished when Lucilius dined with Laelius now has gone underground.