In 1973, Leonard Bernstein gave a series of six lectures at Harvard in which he sought to answer the unanswered question of Charles Ives “whither music?” In the fifth and six lectures he broached the matter of the crisis of the 20th century. Bernstein closes his fourth lecture on the delights and dangers of ambiguity with Mahler’s Ninth “Farwell” Symphony a piece that marked indeed a goodbye to music as Mahler knew it and ushered in a new age of controversy and murky waters. The 20th century looking back had two major crises, which remain unsolved in our 21st century and have thus exploded into the mire we now face both tonally and formally. The tonal schism of the 20th century with, at the seemingly opposite ends of the spectrum Schoenberg and Stravinsky, as well as the formal schism that appears with Cage, Reich, Glass, and a litany of other composers. And now, the advancement of technology ultimately presents a new crisis paired with the sons of unresolved issues of the 20th century, add to this the current generation’s obsession with digital manipulation in a quest to realize “perfect” music. In this lecture, I will touch on the historical and philosophical differences of the aforementioned revolutionaries that have shaped the quagmire in which the modern composer and modern listener now finds himself.