17. The Roots "What They Do" (1996)

Director: Charles Stone III

Rap seemed larger than life in the late '90s. With superstars like Puff Daddy and Will Smith spending millions of dollars on music videos came plenty of impostors trying to emulate the hyper-flashy lifestyle. Someone had to offer commentary on a scene that was spiraling out of control, and who better than a rap group already pigeonholed as "conscious," The Roots? "What They Do" was already a critique of new hip-hop that was straying away from the genre's roots, and its video pushed that notion even further. The clip was full of rap video cliches, and the version with sarcastic subtitles exposing the false realities too often depicted in music videos was a hilarious, landmark moment. But it was also one that found one of their rap idols, The Notorious B.I.G., taking offense to. Needless to say, Biggie had bigger problems, and extravagant rap videos still popped up after "What They Do," but they were never watched without some degree of "psh"-style skepticism in the wake of this one.