Trapped in a context in which capitalism seemed to have colonised all remaining spheres of everyday experience, the ‘Generation X’ of the 1990s appeared to have given up the utopian aspirations of the 1960s. While some embraced the attitude of the ‘slacker’, however, others became involved in ‘alterglobalisation’ protests and debates surrounding a new ‘precariat’. These two figures of the slacker and the loser frame the discussion of precarious practices in this chapter. On the one hand, situating the works of Hirschhorn, Alÿs, Creed and Orozco within contemporary debates concerning failure, futility and apathy points to the ways in which weakness and stupidity were embraced through positive reversals. On the other hand, works by Hirschhorn, Alÿs and Orozco are related to debates surrounding the rising ‘precariat’ of capitalism, new alterglobalised perspectives inspired by Latin America, and a general interest, at the time, in informal labour and architecture, as well as the figures of the nomad and the refugee.