Hustle & Flow: “It's Hard Out Here for a Pimp”

2005 – From Hustle & Flow: “It's Hard Out Here for a Pimp” by Paul Juicy J, Frayser Boy and DJ Paul (wrote music and lyrics)

A song that will live in infamy less for its content than for its creators' palpable joy on Oscar night, "It's Hard Out Here for a Pimp" is a harrowing rap song that manages to be both realistic and optimistic in its depiction of people struggling to get by. The chorus has become legendary, Terrence Howard's (who performed the song) vocals representing the best character he ever played and its Oscar win a continued representation of a change in the Academy (Eminem's "Lose Yourself" had won three years earlier).

Best lyrics: "But I gotta keep my game tight, like Kobe on game night."

What is your favorite of the five? Do you agree with me that "Say You, Say Me," is the best of the bunch and that "I Just Called to Say I Love You" is the weakest? Think Pharrell has a chance at taking home the gold this Sunday?