While the hip-hop battle rages in the background somewhere among black literati, consumers and observers, I nod objectively and religiously to Lupe Fiasco as he creates a narrative that surrounds the personified life of an apartment complex in every component , the legs, the chest, a different aspect of living in the hood. Some would present Lupe as a hip-hop alternative, glorifying his intellectualism and political consciousness, at the expense of demonizing other less academically articulate rap artists. Maybe they deserve it. Perhaps they are poorly educated and uncultured. But does this delegitimize their message? Understanding the messages of many gangsta rap artists is a complex task for those whose lived experiences do not relate. We need to find an alternative way to understand and criticize the music we consider garbage. What do rappers really say? Michal P. Jefferies' work Thug Life provides us with alternative tools to answer this question. I seek to further explore Jefferies' "complex cool" and how it allows a thug's masculinity to include love and other emotional feelings. At the beginning of the work, Jefferies tries to identify what hip-hop is. The most poignant discovery is not so black and white people think differently about its meaning, but what emerged was the recognition that hip-hop was created as a tool to give voice to the feelings of the disenfranchised. This places the birth of hip-hop in the birthplace of disenfranchisement, the neighborhood. Hip-hop functioned as a megaphone, a magnifying glass that candidly told anyone who would listen about the hardship, injustice, and racism faced by those living in America's ghettos. It functioned as a tool to tell the stories of the people who live there in order to build an empathetic conversation... at the center of the card......the ability not only suffers emotionally but candidly expresses this pain. These artists are able to both present this hyper-masculine image and at the same time reflect on its moral shortcoming. It is this apologetic and repentant nature of drug narratives that allows artists to become folk heroes. By telling the story of his drug dealing past and conveying a sense of regret, he is addressing those in the same position as him and in a sense he is delivering a confession to apologize to those he has hurt. With the Jefferies complex, we're cool may view gangsta rappers as more than just nihilistic villains. It may not be the preferred way of portraying the story of life in the ghetto, but it does just that. Even with commercial hip-hop, real feeling slips through the corporate cracks to reveal a gangsta masculinity that is emotionally responsive and aware..