It is often asserted that New York City and comics enjoy a special relationship and that the city’s appearance in comics makes the real-world city legible to readers. Such claims, which are rarely supported with critical examples, generally disregard that different cultural meanings are inscribed upon the city in different representations. This paper argues that to consider in what ways comics make the city legible, it is not enough to note that New York appears in them, but we must also ask what and whose New York is being presented. It does so by presenting a case study of several New York-set comics scripted by Brian Wood. Wood’s bibliography arguably provides one of contemporary comicdom’s most striking illustrations of the generic, thematic, and narrative range of possible comics New York mappings. This paper presents comparative social semiotic readings of Wood’s dystopian activist comics Channel Zero (1997) and DMZ (2005–2012), his action film-style Couscous Express (2001) and The Couriers (2003–2005), and his college tales New York Four (2008) and New York Five (2011). The purpose is to illustrate, through the radically different versions of New York presented in these Wood-penned series, how genre, theme, mood, intended audience, and, to a lesser extent, authorial intention help shape the image and legibility of the city in comics. This will show how representation of New York in comics provides not only a setting, but also a backdrop on which can be inscribed meanings to be read that range from major socio-political critiques to intimate personal reflections.