Amidst the powerfully democratizing, public spheres of Web 2.0, life writing has taken on new geographies and forms of mobility through webcomics. As an experimental mode of self-representation, webcomics are part of an urgent, digital turn in autobiographical writing, where speaking to one’s personal experiences also takes place within the social economies of the Internet. This paper analyzes webcomics as a compelling new dimension of autobiographical illness narrative, using Allie Brosh’s webcomic blog, Hyperbole and a Half, as its case study. Launched in 2009 on the free blog platform, Blogspot, Brosh’s deceptively simplistic aesthetic and comically dark representation of mental illness has since amassed near-cult following online. Drawing on the discipline of life writing and from comics studies, I aim to position Brosh’s webcomics within the field of graphic medicine and to explore how they might expand conventional understandings of illness within this contextual frame. Brosh’s work is a significant precursor to hybrid forms of illness narrative still emerging from digital spaces — this paper asks how webcomics capitalize on both the affordances of the Internet and the aesthetic of comics to connect audiences across vast distances with collective experiences of everyday illness.