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Cicero's late works show frequent and concerted interest in what it means to reconceive of social genres and practices (oratory, politics, friendship) as solitary arts. Through three brief case-studies focused of the rhetoric of solitude in writings from 46-44 BCE—1) in the audience-less oratory imagined by the post-political world of the Brutus (46 BCE); 2) in Cicero’s letters to Atticus from Astura, and their relationship to Cicero's use of the Republican dramatic and historiographic tradition of the solitude of Scipio Africanus; and, 3) in the friendless friendship of the Laelius de Amicitia (44 BCE)—I demonstrate how Cicero's irrepressibly political social orientation (as described in works such as Dugan 2005, Stroup 2010, Gildenhard 2011, Baraz 2012) did not preclude, but rather encouraged, the development of ways of talking about and representing the relationship of individual to society that were in productive tension with the ideals of the vita activa. The tensions I explore can help us unify our understanding of Cicero's interests across generic lines, but can also show us how Cicero could make use of generic differences to put these works in conversation with one another: when it comes to understanding Cicero, genre is good, as they used to say, to think with, but is also good to think through and around. In my first case study, I show how the rhetoric of solitude played an important role in Cicero’s reaction to Caesarian dominance in 46 BCE, most forcefully in his treatise on the history of oratory at Rome, the Brutus. Building on Rathofer (1986), Dugan (2005), and Fox (2007)—who have emphasized, respectively, the way the Brutus embodies Cicero’s political triumph, textual triumph, and ambiguous indeterminacy, and in politically potent ways—I show how the tensions that Cicero develops between the frame-narrative and the content of the Brutus, and particularly in certain inapt comparisons (Brut. 187, 191-2) and digressions (Brut. 299-300), contribute to Cicero’s still haltering effort to reimagine oratory, not as a potent public tool, but as a solitary, verbal, art. In my second case study, I move to Cicero’s letters to Atticus his period of mourning at Astura (Ad Att. 12.9-46), which, for the first time in his correspondence, make spaces empty of others (solitudines) into a (sometimes) positive value, one that could be connected with other values such as epistolary relationships with absent friends, and with literary pursuits. Cicero’s description of himself in these letters as “speaking with the solitude” and “speaking with himself” has to be put into conversation with what I show to be 1) Cicero’s complex use of the under-remarked historiographic, dramatic, and religious motif of Scipio’s solitude, alluded to at both the beginning (De Rep. 1.27) and end (De off. 3.1-2) of Cicero’s philosophical oeuvre; and 2) Cicero’s self-referential description of solitude-seeking mourners in the Tusculan Disputations (3.63-4). In my third and final case study, I show how Cicero’s (Laelius) overtly thematizes the problems of solitude through its narrative frame and through a series of hypotheticals that draw attention to the paradox of conceiving of friendship, after the death of a friend, as a philosophical, and impersonal, virtue. I show how the Laelius actively incorporates reflections on solitude from the Brutus, Cicero’s correspondence, and other Ciceronian texts, and, by bringing these texts together, I show how thinking across generic lines can help us to destabilize certain diachronic readings of Cicero’s corpus. In conclusion, I point to ways in which Cicero's struggles with the rhetoric of solitude can help us open new directions in the study of contemporary Roman religion and society, and, with quick glances at Augustine and Petrarch, in the study of the representation of solitude and individuality in later periods.