This paper discussed the Rubber Band Effect, the tendency in music to evolve into a much simpler form once it has reached a very complex state. To begin, a piece displaying serial techniques was analyzed and compared to pieces that used minimalist characteristics. Then, a piece from the cool jazz era was analyzed and compared to a piece from the bebop era. In both instances, the proceeding musical styles were much more complex than the style immediately following. While many factors played a part in influencing the direction the music would evolve, evidence suggests that the simpler musical styles offered a release and freshness from the complexities of the music before it. One can then assume, perhaps, that this is a natural and reoccurring reaction in music.