What is democracy, human rights, and governance (DRG) program evaluation? This paper defines the subfield, outlines major challenges to undertaking evaluation in highly politicized programming environments, and orients its current state with respect to its historical trajectory. The author describes the pendulum swings DRG evaluation has undergone in methodology, paradigms, and interests, organized into four generations: the Cowboys, the Technocratic Disenchantment, the Messy Middle, and the Complexity Crew. The paper describes how the concept of complexity came to dominate the subfield, emerging out of the importance placed in context and contextual relevance for programs focused on political goals. The author puts forward a framework for operationalizing complexity more consistently within the DRG evaluation sector and concludes with a discussion of current issues and debates in the field.