Content Warning: This section contains discussions of race, racism, racial identity, anti-gay bias, gun violence and fatalities, wrongful conviction/imprisonment, and the foster system.

One idea that Jacqeline Woodson explores throughout the novel is the huge impact that cultural icons such as Tupac Shakur can have on adolescents as they are growing into their identities and thinking about their futures. The events of Tupac’s life and the content of his music are intertwined with the narrator’s and her friends’ own experiences. Not only do they see themselves reflected back in him, but they also see a model for what their lives could become in the future—for better or worse. The way Woodson portrays the girls’ intense connection with Tupac encapsulates a common adolescent experience. Many teens have an icon that is important to them, and even adults might recall a famous person they identified with or idolized during their adolescence.

Just as every individual has their own reasons for relating to a cultural icon, Tupac means different things to different people in the novel. D and Jayjones talk about how he speaks for them and tells their stories. As a child in foster care, D can relate to his feelings of abandonment while his mother was in prison.