This paper surveys a collection of music-related interactions, sanctions, circumstances and figures that embodies the spirit of diplomacy and defiance in the Horn of Africa during the twentieth century. The research will examine historic moments of goodwill, propagation, ingenuity and activism that altered the course of modern music culture in Ethiopia, Eritrea, Somalia, and Sudan, where government officials, cultural ambassadors and, most significantly, musicians wield their authority, influence, popularity, instruments and voices beyond the traditional norms of their enterprise. Along these lines, the paper will discuss the expansive concept of jazz as symbolically appropriated and re-purposed by the performing artist and diplomat associated with the region. Although far from being exhaustive, this work engages with musical activity as a vehicle for information, identity, nationalism and broad meaning.