This article analyses the relationship between cannabis use and educational trajectories among 42 young drug users, recruited at addiction treatment centres in Denmark. Quantitative research shows regular cannabis use to be associated with poor school performance and drop-out. However, these studies do not pay much attention to differences between educational tracks or to the links between the educational field and other fields. Drawing on a Bourdieusian framework we analyse the interviewees' involvement in four different fields: the academic field, the field of vocational schools, the labour market field and the artistic field. We contribute to the literature on post-16 educational trajectories by showing how successful 'investments' in education depend not only on available resources (capitals), but also on the ability to navigate in an increasingly complex educational system. Furthermore, we show how regular cannabis plays into the 'illusio' of different fields, challenging the interviewees' playing of educational games.