In this chapter we explore the histories of our participants’ illegal drug use careers. To begin with, we look at the participants’ initial experiences with illegal drugs, before discussing what happened in the immediate aftermath of this. Then, we will investigate the ‘experimental’ phase of illegal drug use that most participants underwent, where their drugs repertoire widened and where their use became heavier. As we will see, this often took place as part of their engagement in a subcultural movement. Finally, the chapter will turn its attention to the notion of ‘transitions’. We will suggest that the participants’ drug careers have been largely contingent upon their other circumstances at any given time. Transitions (and ‘turning points’) affecting occupational statuses, jobs, places of residence, family situations and health have all played a role in shaping the trajectories of our participants’ drug careers. We end the chapter by suggesting that the transitions experienced by our participants can be properly comprehended only in light of the notion of ‘liminality’. This refers to the sense of radical uncertainty that subjects now face as they make their way through a lifecourse that has lost its normatively ordered sense of stability and direction and leaves them feeling constantly in limbo. In this way we can begin to see the waxing and the waning of illegal drug use over their lifecourse as an inevitable outcome of our participants being repeatedly forced to adjust to an unpredictable series of transitions and turning points.