Critical GIS is a research framework in geography that stands at the border of GIScience and human geography, and has been revolved around the epistemological ground, ontology, and methodology of GIS, and its social impacts. Since Friday Harbor Meeting in 1993 when human geographers and GIScientists began engaging in dialogue and growing climate of discussion, the past twenty years have shown a tremendous growth in efforts to understand GIS and the theory behind it, and an array of creative ways of conducting critical GIS such as GIS and Society, participatory GIS, qualitative GIS, and feminist GIS. These are all, what I consider, evolutions of critical GIS, innovative researches ‘with’ and ‘for’ critical GIS. This paper reviews primary debates and reactions vis-à-vis critical GIS by focusing on its social history and key discussions. I particularly demonstrate that the value and discussions of critical GIS still remain relevant, and seem as important as ever, with new questions and unprecedented digital and spatial technologies such as geographic web, spatial media, spatial humanity, and Big Data.