This book explores how Black-produced films, hip hop songs, and magazines shape the way we think about the African American high school experience. Using critical media literacy as its foundation, the book treats media as a powerful teacher, one that sends messages about race, school, success, and who is expected to thrive. Rather than seeing these images as harmless entertainment, the book shows how repeated media stories help normalize certain ideas about Black youth and education. Qualitative content analysis is used to closely examine popular films, songs, and magazines, looking for patterns in how Black students are portrayed and what education is said to offer them. Beyond theory and method, the book focuses on real-world impact, calling for transformative storytelling that celebrates the diversity and resilience of African American culture while fostering equity in education and media representation. Offering tools for educators, parents, media creators, and students to develop critical media literacy skills, challenge harmful stereotypes, and demand more authentic, complex, and empowering representations of Black youth and their educational experiences, this book will interest scholars and students of media studies, film and TV studies, education studies, cultural studies, African American studies, sociology, and communication studies.