Years before Presidents Barack Obama and Raid Castro announced a "thaw" in US-Cuba relations on December 17, 2014 (17D), Cubans were intensifying ties through the transnational circulation of popular culture. To understand Cuba and its diaspora in the twenty-first century, it is essential that we attend to the transnational networks in place before 17D that continue to shape quotidian life for people on and off the island. I begin in Miami, with the "afterlives" of a comic variety show called Sabadazo-popular on the island during the 1990s-to illustrate how what it means to be Cuban, politically and culturally, has shifted away from the exile generation that arrived in the 1960s and 1970s. I complement this analysis with attention to generational tensions within the diaspora and representations of race and sexuality. I then move to the island to examine el paquete (the package), a terabyte's worth of mostly foreign media updated and distributed across the island weekly. I contend that the economic and cultural impact of el paquete cannot be fully understood without careful consideration of the role of the Cuban diaspora.