Drawn from Merleau-Ponty's embodiment theory and Vygotsky's sociocultural learning theory as conceptual framework, this research investigated how Singapore adolescent students accrued and embodied meaning with school art. Combining the methods of microethnographic observations and phenomenological interviews to document the process of artistic schooling in situ, the author uncovered playful mindfulness among students while they completed the required skill acquisition in Singapore secondary schools. The seemingly paradoxical nature of playfulness and mindfulness merged to demonstrate students' mindset as well as the characteristics of their learning. For the purpose of expansive sociocultural interpretation, three metaphorical themes emerged: a stretch of adolescent artistry, a leap in advancing artful disposition, and a bow to schooling and enculturation. (Contains 5 figures and 5 endnotes.)