The terrorist attacks of September 11, 2001 prompted the government to take drastic political action, such as the War on Terror, and inspired the American people to feel new cultural anxieties. Literature and popular culture also responded to 9/11 with attempts to make sense of such an unprecedented event. This thesis argues that superhero stories, both in comics and onscreen, are particularly well-suited to deconstruct and critique post-9/11 American society through their depictions of power and the question of how individuals with superpowers fit into society. Specifically, this thesis engages with Marvel Comics' Civil War (2006-07), its film adaptation Captain America: Civil War (2016), Dynamite Comics' The Boys (2006-12), and the first season of its television adaptation from Amazon (2019). Through examination of themes including accountability, corruption, and dominance, this thesis reveals how, in recent years, the tropes of the superhero genre have been portrayed in nuanced ways that do not allow for a simple binary between good and evil. As such, these stories reflect the difficulty Americans have faced in adjusting to the realities of post-9/11 America, as actions that were meant to provide security have proven increasingly fallible in the years since the terrorist attacks.