This manuscript is a conceptual article that intends to address 'playful creativity' as an underexplored but potentially insightful component of TESOL programs. To this aim, playful creativity is first defined under a critical purview of traditional and recent conceptualizations of creativity. Afterward, 'creative TESOL' is briefly addressed. 'Pedagogical humor' is next put forth as a practical outlet for playful creativity in language education. To further elaborate on (and operationalize) such creative TESOL, 'humor-integrated language learning' (HILL) is outlined. HILL is argued as an innovative pedagogical approach with far-reaching effects. The article anchors the contention for humorizing creative TESOL in a) the literature-informed benefits of pedagogical humor, b) new directions in creativity programs, and c) the criticality of creativity. Several instructional designs and a sample activity are also outlined to better familiarize readers with this approach. The paper finally addresses practical considerations and further developments in HILL within the framework of playful creative TESOL.