A criticism raised about mediatization research is that although the concept of mediatization presupposes a long-term temporal perspective, there are few projects that have studied the process methodologically over time. This article argues that a generational approach can serve as one suggested analytical solution to the problem of studying long-term social, cultural, and societal change. The article describes a recently finished project on media generations in Sweden and Estonia and discusses overcoming the problem of conducting research on mediatization as a long-term process. Through intergenerational and cross-cultural analysis, the article shows how media memories from childhood and the formative years of youth can reveal specific traits in the historical process and how the role of the media has changed over time in the minds of different generations. The article focuses on four generations that had their formative years during significant historical moments in the late 20th century; these formative moments were marked by specificities both in the respective national media landscapes and in the vast historical and geopolitical differences between the two countries.