This article explored the relationships between the learning experiences and musical proficiencies of a formal and an informal popular musician in Malaysia. The presence and impact of formal popular music education within popular music culture is become increasingly harder to ignore, and while this phenomenon had been examined by numerous popular music scholars, there is a lack of attention towards the implications of learning experience on acquired musical proficiencies. In this study, participants took part in semi-structured interviews that enquired about their music learning histories and musical skills tests that examined their sight-reading, play by ear, and improvisation proficiencies. The aim was to compare and ascertain the disparities between both musicians’ learning histories and musical proficiencies, as well as to identify any potential relationships between learning methods and musical proficiencies. The findings showed that the musicians developed contrasting habitual music-making practices, attitudes and dispositions and musical proficiencies. Furthermore, the informal musician outdid the formal musician in almost all aspects examined in the musical skills tests. Implications from this article include the need for providers of formal popular music education to approach the study of popular music on its own terms, and develop methods of structured learning that enhances the development of virtuosity within the culture of popular music.