The 25 Realest Rap Songs About Prison

2Pac "16 On Death Row" (1997)

Producer: 2Pac
Album: R U Still Down? (Remember Me)
Label: Amaru, Jive

Many rappers face incarceration with world-weary resignation; others are defiant. Tupac's "16 on Death Row" was positively searing. While Nas wrote in an impassive show-don't-tell on "One Love," Pac brought a politically-engaged conscience to the foreground, and that meant confronting incarceration directly and explicitly. It shifted prison from a simple setting to a central point of conflict, laying out the social context, the systemic maze that creates a nation of prisoners. He described a teenage archetype, giving his characters a universal relatability, and delivered his verses with powerful expressiveness, giving "16 on Death Row" visceral immediacy (especially in the description of his cellmate's victimization). But there's an undercurrent of hopelessness, too, at the lack of available options: "Instead of livin' sad in jail I could have died free and happy." David Drake

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