This chapter explores three classical singing teachers' values and beliefs about singing teaching and learning, informed by 400 years of singing pedagogy traditions. Employing Shulman's theory of Signature Pedagogy, (Daedalus: Am Acad Art Sci 134(3):52-59, 2005), I explore how the time-honoured tradition of one-on-one classical singing teaching forms 'habits of the mind, hand and heart'. Through an examination of three case studies of classical singing teaching, I investigate how the life experiences of three eminent teachers have shaped their own practices and how implicit cultural values and beliefs about classical singing have likewise shaped their approaches in the one-on-one lesson. Within classical singing pedagogy and the history of singing, 'singing teachers draw on their personal experiences within an essentially hegemonic oral culture' (Welch et al, Music Educ Res 7(2):225-249, 2005). This chapter illuminates this oral tradition and offers an alternative insight into approaches to singing teaching and learning.