18. UGK on Jay-Z's "Big Pimpin'" (1999)
Album: Vol. 3... Life and Times of S. Carter
Label: Roc-A-Fella, Def Jam
It's fair to say that this track provided the first exposure to the work of Pimp C and Bun B for a number of late-pass rap listeners. Bun proceeds to go all out as he details how he'll steal ya hoe, name checks the Drag Boys' iconic "Drag Rap (Triggerman)" and does his best to encourage literacy amongst vocab-deficient competitors.
Never a crew to shy away from indulging in the occasional expedition into Ignorant Rap territory ("Pregnant Pussy," anyone?), UGK were even able to coax the usually reserved Jay-Z into spitting what he later recanted as something an "animal" might say. Ah, politics as usual.