This article investigates the way Swedish cultural journalists from press, radio and television perceive the core and boundaries of their sub-field at a time when digitalisation and “journalistification” blur them even more. It draws on 27 in-depth interviews with cultural journalists that have worked in the field since the 1980s. What is defined as cultural journalism has expanded since the inclusion of popular culture in its mandate in the early 1990s. Despite this, cultural journalists at different media share similar understandings of their remit, even if self-identification with current practices varies somewhat by generation. The study shows how cultural journalists defend and negotiate the boundaries towards debate and opinion, and news and entertainment journalism. Cultural journalists experience pressure by management to be relevant, newsworthy and “clickable”. Especially press respondents felt that cultural debates have become increasingly indistinguishable from societal debates, due to their visibility in the digital flow. How cultural journalists negotiate boundaries with entertainment and news desks varies somewhat depending on the media organisation. Boundary challenges appear through new genres related to liveness, personality-orientation and societal debate, all of which may conflict with the central task of cultural journalism—to provide in-depth reflection and expertise-based analysis.