The archetype of the cowboy as it was originally conceived in the late 19th century—unyielding, free-spirited, and courageous—may need an urgent revision in the new millennium. Far from destroying the American frontier hero par excellence, the third season of True Detective (2019) and Fallout (2024) offer a more nuanced, sensible, and sociable depiction of the cowboy that points towards the deconstruction of the archetype or, rather, to its updating within the context of the Trump era in corporatist America. In this essay, I analyze and describe how the cowboy myth is stripped of some of his traditional traits, particularly those associated with the relentless use of violence and a masculinity built upon a macho attitude.