19. 2Pac on Scarface's "Smile" (1997)
Album: The Untouchable
Producer: Scarface, Mike Dean, Tone Capone
Of the seemingly endless posthumous Tupac appearances, this collaboration with the legendary Brad "Scarface" Jordan was perhaps his most haunting and introspective, as Pac muses about being "addicted to fatal attractions," before asking, "Somebody save me/Lost and crazy, scared to drop a seed hopin' I ain't cursed my babies."
Not only did "Smile" provide Scarface with his only Top 20 Billboard hit, it also served as a respectful farewell dedication to rap's most influential figure of all time. "Maybe now niggas feel me now, picture my pain/Embrace my words make the world change, and still I smile." Looks like Makaveli had the last laugh after all.