This study was conducted with six classes of third-year students in a male-only middle school. Classroom art therapy with play was conducted for two months, and a total of eight sessions of 45 minutes per session during art class time. Consequently, a total of 48 sessions of art therapy were conducted. The process of inquiry was recorded, recordings were transcribed, and the students works were recorded with photographs. An understanding of the themes was generated using collected data such as questionnaires, observations, interviews, works of art, audio recordings, and video recordings. Efforts to secure the authenticity of interpretation and truthfulness of the inquiry were made through several processes of organizing, analyzing, synthesizing, conceptualizing, and discomposing various data. As a result, the following meanings of the process of classroom art therapy with play were derived. First, classroom art therapy with play gave the body freedom. Second, “you,” “I,” and “we” met through the classroom art therapy with play. Third, the classroom became a playground through classroom art therapy with play. Fourth, young people expressed and experienced democracy in their own way through classroom art therapy with play. Through this study, the researcher wanted to show that life with play is necessary for adolescents, researchers themselves, parents, and professionals working with adolescents.