Playfulness captures individuals’ dispositional differences in (re)framing a situation in an amusing, humorous, and entertaining manner. This study examines how and when highly playful employees may exhibit organizational citizenship behaviors directed to organizations (OCBO) and individuals (OCBI) by drawing on the socioanalytic theory of personality and person-situation interaction models. We suggest that playfulness drives employees to pursue both goals of gaining status (labeled as “getting ahead”) and gaining social acceptance (labeled as “getting along”), which further prompt them to engage in both OCBO and OCBI that align with these goals. We also propose that the positive effects on OCBO and OCBI are realized through highly playful employees’ friendship with their leaders and mitigated by team formalization climate. Multi-source, multi-wave data from 368 employees from 84 teams supported most of our hypotheses. Theoretical and practical implications are discussed.