The hypothesis was that the challenge of performing in and producing one of Shakespeare's plays would give adolescents an experience of rigor and excitement that would enhance self-esteem, would provide opportunities for positive risk-taking, and would encourage pro-social peer-bonding. Working with an experienced youth theater director, a group of 17 middle school students rehearsed, produced and performed a full-length play by Shakespeare as an elective class. The students took a pre-test using the Rosenberg Self-Esteem scale and the students used the same scale as a post-test. An analysis of the pre- and post-test scores showed a rise in self-esteem that was statistically significant. Risk-taking and peer-bonding behaviors were examined through triangulation of qualitative data: daily researcher journal, weekly student journals, and bi-weekly group discussion. The qualitative data supported the findings of the quantitative data in noting an increase in self-esteem. The qualitative data supported the students' taking of positive risks. The qualitative data on peer-bonding was inconclusive.