19. OutKast – "Flip Flop Rock" (Feat. Killer Mike & Jay-Z)
Dungeon Family meets Rocafella, and with a weirder, overall stronger result than on the generic “I Do” that later joined Andre and Jay for the first time. Hov is attacking the outer space drum pattern here, dancing around the tittering hi-hats while talking shit about the S. Dots (I loved those shoes). The long-awaited yet still-unlikely pairing of Jay-Z and Big Boi finds Jay over a beat that sounds like tectonic plates shifting under a seedy strip club in Atlanta, providing a more frantic and refreshing landscape than usual for Jay to skate on.