Despite the moderate success of their predecessors produced during the 1970s and the 1980s, superhero films effectively began to dominate the silver screen and shatter global box offices with the release of Bryan Singer’s X-Men (2000). As they shifted from campy escapism to thoughtful dialectics on contemporary issues, superhero films were inarguably affected by the 9/11 terrorist attacks which severely fractured all aspects of American identity and life. Twenty years later, there is no shortage of superhero films which have implicitly or explicitly grappled with the trauma 9/11 induced, as well as its ramifications concretized by the ceaseless War on Terror. Yet the necessity to gauge the imprints of these decades of disruption on popular culture does not seem to be abating, as purported by Zack Snyder’s Man of Steel (2013) and Batman v Superman: Dawn of Justice (2016). Therefore, by examining the films’ post-9/11 urban and psychological wreckage, this thesis first examines the traumatized state of the films’ characters as interrelated with metropolitan destruction in the wake of a historically-redefining tragedy. Taking into account that the titular films coalesce into a singular narrative, the thesis examines its socio-political subtexts with causal links to and a commentary on the post-9/11 American milieu. Finally, the thesis approaches the post-9/11 superhero films as both pop-cultural artifacts and coping mechanisms, aiming to show how Man of Steel and Batman v Superman: Dawn of Justice remediate the wounded American psyche rather than reinforce its paralysis in the twentyfirst century.