Song: "Keep Ya Head Up" (1993)
Album: Strictly 4 My N.I.G.G.A.Z.

Adapting an old adage, and flipping in on its head? Not something enough rappers are capable of, let alone inverting years of white supremacy with a bold statement that called upon history at the same time. And for Tupac it wasn't just enough to do that—to take an explicitly racial confrontation and turn it into the compelling start of one of his most poetic ruminations—but he needed to do it effortlessly, too.