Recognizing the serial, fragmentary, and revelatory nature of the self accounting prevalent in digital media networks, this dissertation explores a particular mode of autobiographical discourse that is often overlooked by scholars: the diary. Often associated with teenage girls and queer subjectivity, the diary has been pushed to the margins of literary history and is often read as documentary evidence of history, rather than an aesthetic mode of autobiography. This same dynamic is true of diaristic discourse in contemporary social media, which is derided as frivolous while it is simultaneously scrutinized as an authentic record of the subject. Responding to the rhetorical demands for authenticity and consumability that structure networked sociality, the examples of self accounting considered here mobilize diaristic discourse and its affect of veracity, while simultaneously creating a visual spectacle that affords cultural legibility by way of virality. The individual chapters telescope from the present to the past in order to trace changes in the meaning and materiality of the public sphere, and the parallel development of authenticity as an affective register of cultural legibility for autobiographical productions and, by extension, the individuals producing them. The key images of self-reflexive accounting in my analysis include contemporary examples such as the lonelygirl15 vlog, diary films, and the transmedia cue card confession trope as well as resonant historical examples in nineteenth-century photography and fiction, as well as the early twentieth-century social autobiography project Mass Observation. Through close readings of both the aesthetics and materiality of these productions, I argue that the transhistorical reflexive grammar of the diaristic mode in visual new media is characterized by the foregrounding of editing techniques, an interrogation of ‘reality’ as a genre, and a DIY aesthetic that foregrounds the constructedness of the spectacle rather than the veracity of indexicality. What this dissertation offers, then, is a historically informed analysis of social media practice that attends to the significance of its communicative and aesthetic functions. In the process, it illustrates how contemporary discourses of surveillance emerged, in part, from this mode of self accounting and were thus incorporated into the material structures of networked sociality.