The youth media movement, which now has a place in countless venues, communities, and scholarly discourses, reflects an evolution of practices pioneered in the 1950s and 1960s as amateur filmmaking increasingly became a reality in American families and schools. In this paper, we examine the films of Robert J. Clark, Jr. as a representative early example of predominant modes of expression within the youth media community. We seek to identify the links between past and present in the continued popularization of youth media practices in schools, after-school learning environments, and camps as an issue of significant importance for archivists and historians, communities, and schools. This paper examines the historical development of a youth media practitioner who worked in both a school and an after-school learning environment for over 25 years, beginning in 1970 and continuing to 2005. We conducted a study of narrative feature-length films created by children ages 9-17 from a private archive of youth media work collected by the founder of Cinekyd, a for-profit youth media project developed in Philadelphia by Robert J. Clark, Jr. In this paper, we track the evolution of four films created between 1976-1982 as both historical film objects and as evidence of learning experiences. Though its amateurishness can often be strange, even off-putting, to wider audiences (one reason why much youth media is rarely showcased and often discarded upon completion), youth media and documentation of its creation also offer insights on the relationship between children and their adult mentors and between youth media authors and their presumed and real audiences.