26. Outkast "Elevators" (1996)
Director: Michael Martin
The video for "Elevators (Me and You)," the lead single off Outkast's sophomore album ATLiens was the first inclination that the group was maybe getting a little strange. In it, Andre 3000 and Big Boi graduate from high school, after which Andre trades his cap and gown for a turban, and the group drops out of society at large, fleeing the city for a woodland spiritual cult sojourning toward a pyramid-entrenched promised land. It was a radical shift away from the fun-loving teenage wrecklessness of their early years and the first step toward the oddball Southern mysticism they'd come to be known for.