The article presents the general principles underlying the author’s program for studying in detail the political socialization of high school students. The program had been launched in 1996, and the results were published in a monograph entitled ‘High School Student in the World of Politics’ (1997). The basic purpose of the program is not simply to look at the modern Russian political landscape through the eyes of a teenager, but to use this view to bring into relief the actual contradictions and tensions of Russian political life. This is based on the understanding of the particular culturological significance and status of teenagers, and of their uniqueness in the general culture. Moreover, the author believes that teenagers’ opinions sometimes reflect sociocultural tensions more precisely and in more detail than do those of adults. The second large survey in the framework of this program was carried out almost a decade later, in 2005. The concluding part of this article compares the responses of the two generations of teenagers that deal with various aspects of Russian politics. The author’s goal is to determine shifts in values that influence the trajectory of changes in teenagers’ perception of political issues.