Anyone interested in philosophical argumentation should be prepared to study philosophical debates and controversies because it is an intensely dialogical, and even contentious, genre of argumentation. There is hardly any other way to do them justice. This is the reason why the present special issue addresses philosophical argumentation within philosophical debates. Of the six articles in this special issue, one deals with a technical aspect, the diagramming of arguments, another contrasts two moments in philosophical argumentation, Antiquity and the twentieth century, focusing on the use of refutation, and the remaining four analyze particular philosophical controversies. The controversies analyzed differ significantly in their characteristics (time, extension, media, audience,…). Hopefully, this varied sample will illuminate some salient aspects of philosophical argumentation, its representation and variations throughout history. We are fully aware that, given the scarcity of previous studies of philosophical debates from the perspective of argumentation theory, the following specimens of analysis must have several shortcomings. But it is a well-known adage that the hardest part is the beginning. That is what we tried to achieve here, no more, but no less either.