This article brings together two cases to contribute to the growing body of literature rethinking the study of international relations (IR) and the Global South: The Libyan Arab al-Jamāhīrīyah and the Bolivarian Republic of Venezuela. Drawing on media representations and secondary literature from IR and international political economy (IPE), it critically examines three main conceptual theses (authoritarian, rentier, and rogue) used to describe the historical socio-political formations of these states up to this date. Mixing oil abundance with authoritarian revolutionary fervour and foreign policy adventurism, Libya and Venezuela have been progressively reduced to the figure of one man, while presenting their current crises as localized processes delinked from the imperialist inter-state system. The article argues that these analyses, if left unquestioned, perpetuate a US-led imperial ordering of the world, while foreclosing and discrediting alternatives to capitalist development emerging from and grounded in a Global South context. In doing so, the article contributes to the growing and controversial debate on the meanings and needs for decolonizing the study of IR.