This chapter offers a more nuanced portrait of the movement, considering the cultural ramifications of activism and the many different ways politicization was experienced by this new generation of Uruguayan leftists. First, it suggests that diverse understandings of leftist activism tended to both encourage and blur the meanings of heroism as expressed in the image of Che Guevara, among other icons of the time. It also traces the individual trajectories of a handful of young people who took part of the mobilizations to show how many of them came to politics only after participating in the era’s countercultural undertakings, such as fanzines, beat festivals, and poetry concerts, which picked up on the main themes and gestures of the global counterculture. In addition, the chapter uses class and gender as lenses through which to understand the meanings of political engagement and cultural participation.