43. Digital Underground "The Humpty Dance" (1990)
Director: Dan Rodriguez
According to Rolling Stone, it was the song that saved the summer of 1990. But it was the video that turned it up. Digital Underground leader Shock G had already appeared as an eyebrow-raising character in a previous clip for "Doowhatchalike," but the name of Humpty Hump or his dance still hadn't burned through American pop culture until the clip for this song emerged. The Groucho Marx glasses with the fake nose. The white fur hat with the tag on it. The women who gravitated towards him not in spite of, but-mystically-because of his "looks." And that dance. That dance. It wasn't just the kind of hilariously, not-even-remotely-self-conscious, absurdly fun rap moment you don't see anymore (as gangster rap's self-seriousness had already started the obliteration of this kind of thing in contemporary hip-hop), but it was also and still remains a visceral, brilliant piece of pop art with an indisputably positive message: Just do you, no matter how freaky. And if that's not enough to convince you how fly the "Humpty Hump" video is, a young Tupac Shakur is visibly dancing in the background. It doesn't get any more classic than that.