This is a transnational cultural history of the charro horseman in Mexico and the United States. It begins with an analysis of the archetype in nineteenth century art and literature, exploring various works of visual and literary culture. The dissertation continues with the popularization of the image through the spectacle of mass entertainment and the emergence of celebrity through bullfighting. This study crosses the border with performers of the secondary acts of Mexican bullfighting in the Wild West shows of the United States. As some of the first migrant laborers who crossed into the United States on railroads, these trick riders and ropers left a significant impact on popular culture north of the border. With the expansion of industrial cinema in the 1920s, Wild West show performers transitioned to film where they spread the image of rope-wielding charros much wider than before. The career of Leo Carrillo parallels many of the political and social developments that allowed the charro archetype to function like a tool of cultural diplomacy between Mexico and the United States. Finally, the appropriation of the image by elite charrería rodeo associations and the post-revolutionary state made the figure a national symbol that unified diverse regions and ethnicities of Mexico. The symbol lost potency as post-revolutionary governments aged and accusations of corruption, fraud, and repression increased, allowing youth in the counterculture to re-appropriate the image as a critique against the state. Today, the image remains an important marker of cultural identity for communities on both sides of the border.