In Italy, the percentage of adolescents dropping out of school is really high. According to several studies, extra-curricular activities can promote dropout recovery. The "Maestri di Strada" Association carries out socio-educational projects in Neapolitan suburbs, by countering school dropouts even through art education. Among several workshops is that of theatrea powerful educational tool, which supports identity and empowerment. The present study aimed to document and evaluate the multi-year workshop journey of a group of adolescents, by giving them and their educators a voice through semi-structured interviews. The latter were conducted with 9 pupils at the end of the penultimate year (Ad-T1) and of the last year (Ad-T2) of their journey and with 3 of their educators (theatre experts) a year after the end of their journey (Ed). The large textual Corpus collected was subjected to Thematic Analysis of Elementary Contexts (T-Lab Plus). The findings (Ad-T1: 6 cluster; Ad-T2: 5 cluster; Ed: 6 cluster) show that both adolescents and educators agree to consider this workshop a precious space where one can reclaim their own desire to learn and grow. Notably, in T1, pupils emphasize differences between theatre and school, their meaningful relationship with educators, learning to regulate emotions and to cooperate, and the alliance with families and the local community. In T2, pupils emphasize the importance of the group, the personal experiences had in each staged performance, and their new idea of adulthood. Similarly, educators regard the group as fundamental, as well as the relationship between the school and the local community, and future prospects.