The concept of “information” in association with music recently re-emerged in music psychology and cognition in the form of statistical learning and as the basis for models of music perception. The first time music and information were associated in a systematic manner was in the 1950s and 60s when, particularly in North American music theory, researchers applied concepts from information theory to analysis and composition. Among the work of the 1950s was Edgar Coons’ and David Kraehenbuehl’s Information as a Measure of Structure in Music (1958). The authors suggested that information could be developed into a useful compositional tool that would aid decisionmaking in terms of form, but would not hamper the composer’s personal style or freedom of choice with regards to musical materials. In this article, the fundamental concepts behind the development of a musical information theory are outlined, giving some simple examples of its possibilities and proposing directions for future development. The outline embraces the necessity for a contemporary musical theory to combine formal, scientific methods and an awareness of contexts and relationships inspired by the New Musicology and the study of music as a cultural activity. As a theory of communication, information theory is presented as a far more subjective and pliable concept than is implied in Claude E. Shannon’s Mathematical Theory of Communication (1948), the work upon which many of the musical information theories in the 1950s were based. A flexible view of information theory and the concept of information must be maintained to enable them to take part in contemporary musicological discourse.