In this article I explore the notion of jazz cosmopolitanism in Malawi in an effort to examine the complexities of navigating transnational multicultural spaces. I am specifically interested in how this plays out in southern Africa, where the music industries are affected by ongoing influences from the Global North sedimented on top of a history of multiple types of colonialism. I outline some foundational works on music and cosmopolitanism in Africa before discussing the music and career of Malawian jazz guitarist and producer, Erik Paliani. Paliani stands apart from many Malawian musicians based on his career highlights, but also his commitment to jazz as an international and African art form as well as a means of navigating the world. I focus on two compositions as performed by him in order to explore creativity and positionality as they relate to the intersection of jazz and African musics. I also interrogate my own positioning as a foreign white male and frequent participant in the Malawian music industry since 1991. In doing so, I unpack some complexities to cultural representation in cosmopolitan African spaces articulating with discourses on mobility and privilege. My aim is to understand how reconciling individual expression and collective belonging may be accomplished through the praxis of Afro-jazz in southern Africa. I suggest that jazz cosmopolitanism, rooted in socio-musical practices in southern Africa and beyond, adds a crucial layer of expressive devices and referential frameworks that illustrates important stories of human experience in this region.