This article discusses from an inter-cultural and inter-generational perspective the relationship between ‘objective’ media landscapes and how they are subjectively perceived among four different media generations. Based on a focus group study with media users in Sweden and Estonia of two tentative generations, the relationship between the ‘objective’ and ‘subjective’ media landscapes is analysed, as is how the landscapes produce nostalgia at the intersection of age, generation, life course and life situation. Based on the differences found in the cross-cultural and the cross-generational comparison, it is concluded that in relation to the formative years of the respondents, there are two different kinds of nostalgia produced: one individually based, focussing on childhood memories; and one social or collective, focussing on the formative years of the respondents.