As musicians, we have been taught to idolize certain figures in music history. These individuals are considered untouchable, unassailable, and unquestionably brilliant. This practice is increasingly evident in jazz. Figures like Duke Ellington, Louis Armstrong, Charlie Parker, and Miles Davis have all undergone a virtual apotheosis. While there is no question of their importance, the idolization of these people makes attaining what they have done difficult to grasp. We have dug a chasm between aspiring musicians and the music itself. This gap is wide in that we regard these figures and their music so glowingly that relating to them becomes difficult. Students must understand that these figures were ordinary people. Through technology and creative storytelling, students can explore the world in which these musicians lived. Providing context can help students gain a better understanding of how jazz music has evolved and why. Students can then use this knowledge to develop confidence in their creative process and in how it relates to their unique life context.