Media in the 21st century are changing when, where, what, and how young people learn. Some educators, youth researchers, and parents lament this reality; but youth, media culture, and learning nevertheless remain entangled in a rich set of relationships today. These relationships and the anxieties they produce are not new; they echo worries about the consequences of young people’s media attachments that have been around for decades. These anxieties first appeared in response to the fear that violence, vulgarity, and sexual desire in early popular culture was thought to pose to culture. Others, however, believed that media could be repurposed to have a broader educational impact. This sentiment crept into educational discourses throughout the 1960s in a way that would shift thinking about youth, media culture, and education. For example, it shaped the development of television shows such as Sesame Street as a kind of learning portal. In addition to the idea that youth can learn from the media, educators and activists have also turned to media education as a more direct intervention. Media education addresses how various media operate in and through particular institutions, technologies, texts, and audiences in an effort to affect how young people learn and engage with media culture. These developments have been enhanced by a growing interest in a broad project of literacy. By the 1990s and 2000s, media production became a common feature in media education practices because it was thought to enable young people to learn by doing, rather than just by analyzing or reading texts. This was enabled by the emergence of new digital media technologies that prioritize user participation. As we have come to read and write media differently in a digital era, however, a new set of problems have arisen that affect how media cultures are understood in relation to learning. Among these issues is how a participatory turn in media culture allows others, including corporations, governments, and predatory individuals, to monitor, survey, coordinate, and guide our activities as never before. Critical media literacy education addresses this context and continues to provide a framework to address the future of youth, media culture and learning.