The paper introduces a set of four studies focused on adolescents in the Czech Republic. In the first part, authors reflect on the cultural background, the political, social, and psychological factors that have had influence on several generations of adolescents in the period of the communist totalitarian regime. They also describe the social changes brought by the democratization of Czech society since the early 1990s. Second part of the paper reviews the life and changes in the behavior of Czech adolescents over the past 20 years. Based the findings of three studies representing three cohorts of adolescents (1992, 2001, 2010), it is argued that current Czech adolescents are becoming more like their Western peers. Compared with the 1990s adolescents, the current cohort is more realistic in their expectations, oriented more on achievement, social pleasure, and material values. Their relationship to formal authorities is weaker; especially, the relationships with parents and teachers are more liberal.