Jon Gilgoff is the Boys Services Manager of the Youth Justice Institute in Oakland, California, and a former Robert Bowne Foundation Fellow who researched Boyz 2 Men through his work with the Educational Alliance in New York City. Boyz 2 Men aimed to provide a positive alternative to drugs as a means of coping with the multiple challenges young men faced as they moved into their manhood in the inner city. Participants had fallen into substance abuse. Many had also joined gangs and already were involved in the criminal justice system. In some inner cities, homicide is the leading cause of death among minority adolescent males (Foy & Goguen, 1998). In this dire context, the struggle simply to keep young men of color "alive and free" (Marshall,2005, p. 1) into their adult years is a challenge. Boyz 2 Men was one gender-based program that aimed to build boys' resilience in the face of such dangerous realities and to help them examine their socialization as males. It created a safe space in which participants could freely express their hopes and fears, supporting one another toward a safer and healthier manhood. This article discusses Gilgoff's experiences as facilitator of Boyz 2 Men and illustrates both the promise and the challenges of such efforts. Gilgoff examines the ways in which the group helped participants explore both the pressures and privileges of growing up to be a man in the "hood", and how for some this process led to fuller expressions of self and increased responsibility in their treatment of others.