#6 “Shed So Many Tears” – 2Pac
What separated the late, great Tupac Shakur from so many of his peers in gangsta rap was his thoughtful, introspective side. And no cut showcases that side better than this pensive single from his somber masterpiece Me Against the World. Released while he was in prison & shortly after he was shot, it struck a chord with fans that still resonates—as does the entirety of his legend.