Recent avenues of exploration in cultural studies reveal new possibilities for a reading of masculinity in Persian Gulf War and Iraq War narratives. There has been much debate regarding the impact of technology on the soldier’s sense of self, exploring ideas of speed, distance, and the possibilities and drawbacks raised by cyborg theory. What is yet to be fully explored, however, is how these factors have affected the trajectory of masculinity which has been thoroughly mapped through the wars of the twentieth century, and can be extended to encompass the literature of these conflicts. This article examines the ways in which masculinity is represented and challenged in Gulf War and Iraq War narratives, specifically Anthony Swofford’s Jarhead: A Marine’s Chronicle of the Gulf War and Other Battles (2003), Tom Paine’s The Pearl of Kuwait (1997), Colby Buzzell’s My War: Killing Time in Iraq (2005) and Evan Wright’s Generation Kill (2004). It explores how the literature of these wars can be read as portraying the impact of technowar on the masculinity of soldiers in the Gulf War, and the return to the post-Vietnam style ‘manly man’ in the later Iraq War. Crucially though, it explores how these narratives complicate such a simplified analysis and identifies the ways in which the technological circumstances of each conflict impact on representations of masculinity at both an individual and collective level.