Drastic changes in student demography, cultural realities and employment outlook in America have added much impetus to the fast-growing interests in Culturally Sustaining Pedagogy (CSP) (Paris, 2012) amongst educators. A recent literature review reveals that a growing number of music educators have jumped on the bandwagon to “liberate [music] curricula” and to “reimagine what music education might look like without the shackles of coloniality” (Rector, 2025). Good-Perkins goes so far as to call for a stop to “hegemonic music colonialism and musical genocide” (2021b). The CSP activist agenda aside, the movement does address a general challenge that educators face, namely the gap between school curriculum and what students come with in terms of their “assets” and learning interests. Good-Perkins (2021a) has described students’ cultures as “fluid, emergent, and an amalgamation of multiple facets of their identities”. Minding this dynamic gap is therefore a challenge for all educators.Over the years, I have developed a culturally relevant and responsive approach (Abril, 2013; Lind & McKoy, 2016) to teaching pre-service music teachers music theory that embraces non-western music. The student teachers that I teach will soon be from the alpha generation, which is deemed “more culturally diverse compared to the former generations” (McCrindle & Fell, 2020). Given the broader societal changes in demography and musical landscape in Singapore, there is a need to look beyond relevance and responsiveness (CRP), albeit for a different set of reasons from the North American situation. I therefore adopt and adapt the CSP lens to reimagine the teaching of music theory to the alpha generation in Singapore.After explaining the essential differences between CRP and CSP as well as presenting the profile of the alpha generation in Singapore, I will share how my earlier CRP-inspired music theory course for pre-service music teachers have morphed into one more aligned with CSP, with attendant changes to assessment practices. I will also reflect on how my underlying musical epistemology (Good-Perkins, 2021a) has changed and explain why the Singapore context calls for additional considerations for bridging the different music theories for the student teachers.