Jazz continues, into its second century, as one of the most important musics taught in public middle and high schools. Even so, research related to how students learn, especially in their earliest interactions with jazz culture, is limited. Weaving together interviews and observations of junior and senior high school jazz players and teachers, private studio instructors, current university students majoring in jazz, and university and college jazz faculty, I developed a composite sketch of a secondary school student learning to play jazz. Using arts-based educational research methods, including the use of narrative inquiry and literary non-fiction, the status of current jazz education and the experiences by novice jazz learners is explored. What emerges is a complex story of students and teachers negotiating the landscape of jazz in and out of early twenty-first century public schools. Suggestions for enhancing jazz experiences for all stakeholders follow, focusing on access and the preparation of future jazz teachers.