This chapter discusses how US hip hop artists justify their participation in State Department–sponsored programs given hip hop’s traditional oppositional, anti-government stance. Many factors motivate artists to participate. Artists cite this work as an opportunity to travel; teach; encounter different cultures; represent their country, culture, gender, race, ethnicity, etc.; and build global hip hop community. This chapter considers whether these artists can be considered complicit with the actions of the government, whether they can act subversively, and whether they can do both at the same time, embodying what can be called subversive complicity.