While many teachers of music composition have influenced both the aesthetic and eventual success of their students, few have equaled the contributions of Arnold Schoenberg and Nadia Boulanger in the twentieth-century. A larger volume of a more comprehensive collection including all music composition teachers of the era would serve a certain purpose. However, the unique aspect of the current text examines, in detail, and herein presented for the first time in print, many of the teaching materials and approaches of these two famed musicians. Selection of these two teachers for comparison was made owing to the musical position so famously attributed to each: Schoenberg’s predilection to the German School; Boulanger’s favoritism to the French/Stravinsky aesthetic. In making the case for both Schoenberg and Boulanger, the Author has chosen two differing philosophies of music education practice of the late twentieth-century and early twenty-first century: those of Bennett Reimer and David Elliott. The Author examines the materials and methods of each Schoenberg and Boulanger in light of each Reimer’s and Elliott’s case for music education philosophy. Among the subjects discussed: the nature of musical creativity, the process and methods of teaching creativity/music, and the teacher/student dynamic, to name a few. In closing, the Author has presented his own suggestions for teachers, or would-be teachers, of music composition in a seven-step process leading to an effective pedagogy of the subject.