This article traces divergent approaches to democracy in the history of anarchist thought. It outlines an anarchist critique of democracy, a defiant composition arrayed against authority, representation and majority rule. Put in contrast to that approach is the anarchist reclamation, the understanding of anarchy as democracy radicalized. The article shows how the critique of democracy typifies classical anarchist thought, while reclamation of democracy breeds in post-classical anarchism after 1939. Yet these lines of thought also coexist historically, and they both continue into our days. Anarchism is now depicted in terms of radical democracy, while a reclaimed critique once again dissociates anarchy from democracy. In an attempt to recognize dialogue between them, this article suggests that divergent approaches articulate an impossible argument that could further the route toward anarchy.