The trilogy of Spider-Man feature films (Raimi, 2002, 2004, 2007) is set in New York, although it is neither an historically accurate representation nor the comic book version, but a third cityscape which imaginatively borrows and builds on both of these precursors. This chapter argues that within that context, the Spider-Man films enact a form of artificial mourning, acting as a popular cultural arena in which some of the immediate tensions and traumas of the post-September 11 Western world are articulated and explored. From the outset, it is important to flag that the term artificial mourning is not necessarily positioning mourning facilitated through popular culture as ‘unreal’ or necessarily ‘less’ than trauma in the ‘real’ world. Rather, the ‘artificial’ in this term is consistent with deploying the artificial not as a marker of the unreal, but rather as a signifier of unstable boundaries, where easy binary divisions no longer make sense. The artificial blurs the divisions between human subject and technological object, between entertainment and politics, and between good and evil. Artificial mourning is an invitation to engage with the Western world’s ‘Long September’ in myriad forms rather than via a single solution or perspective on those tragic events. It is with those ambiguities in mind that the Spider-Man films come into focus as character, franchise, and cultural icon. Spider-Man’s artificiality is evident in the seeming incompatibilities of being both a human subject and a technological object, being both a hero and an everyday person with everyday problems, and being both a means of escapism for audiences, while engaging on some level with serious political and cultural concerns. Moreover, the movies situate Spider-Man and his various nemeses as artificial people in that they are products of substantial technological transformation, whether purposefully or through accidents. Ideas and meaning not only are negotiated at the level of narrative, but also are realised through the connectivity of Peter Parker and Spider-Man with technologies and through the computer-generated imagery (CGI) of the visualised New York cityscape itself.