This paper examined representations of medicinal cannabis users in UK newspapers, 1990–1998. It is important to understand the significance of these newspaper articles during this early stage of the growing cultural normalisation of medicinal cannabis use, in the UK, which is not documented in the existing literature. This is a very different period in relation to access to information for members of the public because it was before the widespread use of the internet. The significance of these dates is also that I started interviewing medicinal cannabis users in 1998, which led to Coomber et al. (2003). Very significantly, almost half of the participants in that article indicated that newspapers were the source of the idea that cannabis was medicinally useful and that this accounted for why they began to use it medicinally. What was in those newspaper articles that encouraged this view? In the current article, I examined 60 newspaper articles about medicinal cannabis use, using a thematic analysis which also draws on aspects of critical discourse analysis. I report on the process of symbolic boundary work which negotiates the ambiguity of individuals portrayed as social insiders but who used cannabis. The representations within the articles emphasized the social insider characteristics of medicinal cannabis users, emphasized their genuine illnesses/impairments, but interestingly also articulated misunderstandings by the journalists which contributed to a positive portrayal.