Researchers interested in the impact of media on the adolescent audience often use content analysis as a first step in assessing the kinds of messages available in mainstream media. These content-analytical studies typically sample from prime-time television programs, blockbuster movies, or top-selling video games. But do these samples accurately reflect the media content to which teens are exposed? The sheer increase in the number of media types and information sources available to teen audiences has opened up a wide variety of options to choose from. This proliferation of media technologies has brought about dramatic changes to when, where, and how adolescents access media content. In this chapter, we provide an overview of our efforts to assess teens’ exposure to media content and the challenges we have encountered in developing our measures. Specifically, we present data from an exploratory study which illustrates that adolescents are growing up in a multiple-media environment, much of adolescent media use is idiosyncratic, and their media encounters are increasingly “interactive.” Content analysis methodology needs to adapt and adjust to these revolutionary changes in the media ecology. We propose an audience-centered, media-ecological approach to content analytical research in response to this emerging interactive new media scenario.