This chapter opens with a brief discussion on the concept of cultural legitimacy and what we mean by the processes of legitimization and popularization. It explains how common the aesthetic evaluative content in our quality newspaper culture sections is in the first place and how it varies through time and across newspapers and articles on different art forms. In the background of the concepts of legitimization and popularization, both referring to temporal processes, there are obvious, respective root concepts: popularity and legitimacy. The chapter presents a qualitative analysis of the evaluations of pop-rock and classical music articles to identify whether the argument about the legitimization of popular culture and popularization of highbrow culture holds up. The peculiar feature of Helsingin Sanomat is the very limited pop-rock coverage in 1990. In the 2000s, pop-rock coverage exploded in Helsingin Sanomat to correspond with the level of the other reviewed newspapers.