This article discusses current challenges towards the essay genre due to medialization of the public sphere. Up until recently, the essay has been strongly associated with the written and printed word, but essay theorists of later years have suggested that an “essayistic mode” can be traced in several other media, including radio and film. In this case, comparisons are made between Spanarna, a Swedish radio talk show broadcast on public service radio since 1988, and a few examples from the written essay tradition. The article takes a closer look at a special feature connecting Spanarna with the written essay: the paradoxical wish to communicate directly with the reader or listener despite the apparent constraints of the media apparatus. It is suggested that this communicative and sociable vision, expressed through the interplay of oral and written discourse, may be one possible ingredient in an essayistic mode that goes across the ages and exceeds different media.