The settler colonial history of America is an intrinsically lonely one, and thiscan be seen by looking at the colonization of the American West, and the newfound masculineidentity which arose from it: the cowboy. American colonialism is a wretched history, but notonly has it devastated the Indigenous peoples who were eradicated and exterminated, so too,albeit in different ways, has the history of colonialism negatively affected the live of thecolonists who inhabited what is now the United States. This is evident in many popularrepresentations of the American cowboy, an iconic figure that arose from the settlement of theAmerican West, but one whose very status is both intrinsically masculine and lonely, a dualitythat is necessarily imposed on the cowboy due to the figure's direct relationship to colonialism.Through looking at two fictional settlers of the American West, the kid in Cormac McCarthy's Blood Meridian( 1985) and Ennis Del Mar in Ang Lee's Brokeback Mountain (2005), this article argues that ineach respective text the protagonist's cowboy-like identity, due to its roots in colonialism,complicates American masculinity and makes the life of the “masculine" cowboy an inherentlylonely one.