In this chapter, we propose creative critical listening as a musical creativity and pedagogical tool and consider the following questions: How is popular music analysis best delivered in a popular music degree which is grounded in diverse creative practices? And how can students be convinced of its value? The first of these questions is addressed in an analysis of the structure of the Bachelor of Popular Music degree at Griffith University's Queensland Conservatorium of Music (Australia). The second is approached through the discussion of data from a targeted student survey, drawing on psychology literature related to the development of expertise. It is argued here that creatively taught semiotic analysis, as the theoretical underpinning of these courses, reinforces the principle underlying the creativities inherent to the pedagogical design of the degree -to replicate, and accelerate, what successful musicians do through reinforcement of creative listening skills. The degree was designed with the aim of developing diverse musical creativities, central to which, it is argued in this chapter, is critical listening, a musical creativity in itself(see Burnard, 2012).