This chapter presents the results of a mixed methods exploratory study assessing the therapeutic potential of using Rap music as an intervention intended to promote resilience and hope among at-risk youth. Forty-two middle school students participated in a program called, ‘Wrapped in Resiliency.’ A pretest/posttest experiential design using the Trait Hope Scale (Snyder et al., 1991) and the Strengths and Difficulties Scale (Goodman, 1997) compared outcomes of youth that attended five Wrapped in Resiliency group sessions. The students were recruited through participation in a summer school program called Century 21. Paired sample t-test results derived from the Hope Scale found that there were no significant differences in means for the Hope Subscales (agency and pathways), or the total Hope Scale. There were also no significant differences in means for the Strengths and Difficulties Subscales (emotional symptoms, conduct problems, hyperactivity, peer problems, and pro-social behavior)or the total Strengths and Difficulties Scale. Qualitative analyses found that the participants were aware of their strengths, possess well thought out coping strategies for stress, and have identified individuals, attitudes, and coping strategies to overcome issues associated with being at-risk. These results partially support the hypothesis that at-risk students possess strengths and resources, as well as the importance of helping professionals understanding and developing interventions that focus on the strengths these youth possess. Implications for clinical practice as well as future directions in research are discussed.