This article analyzes the controversy caused in 2017 by US rapper Wiz Khalifa's narco-tour photos in Medellín, Colombia. Narco-tours are day-long excursions through the mobster Pablo Escobar's landmarks in the city: his properties, the neighborhoods he built, and the roof where the police killed him after years of waging war against the Colombian state. Unlike the polemic films and series on the Colombian drug lord, the Wiz Khalifa controversy was the first time an outcry about the depiction of Escobar was aimed at a US Black artist, particularly a rapper. The outraged reaction exhibited by politicians, audiences, and the national media reveal an unexplored archive of exchanges, miscommunications, and negotiations between, on one hand, a long list of hip-hop household names—including Jay-Z, Nas, Kanye West, Lil Wayne, and many others—who have incorporated the image of Escobar in their music, lyrics, aesthetics, and rhetoric and, on the other hand, Colombian institutional memorialization of the war on drugs. The author argues that Wiz Khalifa's pictures exemplify how mainstream hip-hop brings together the images of the Black American “hustler” and the Latin American “narco.” The juxtaposition of these two images is a denunciation of the similar conditions in Colombia and the United States that force people into the trade as well as a complicated and gory representation of the neoliberal ethos Escobar represents. The article concludes by registering how hip-hop's artistic uses of “Pablo”—as Escobar is known in the genre—clash with Colombian elites’ iconoclastic and moralistic stance in opposition to any representation of Escobar in the media.