Easily one of the most brilliant hip-hop videos of all-time, The Pharcyde's "Drop" was a bit of a head-scratcher when it was first released. It popped up on the weekly rap video countdowns, and most viewers couldn't help but say, "How'd they do that?"
Basically, the whole video was filmed backwards, in sync with a version of the song that had the lyrics also playing backwards. The group literally learned how to say the lyrics to the song backwards for the video shoot, with the help of a for-hire linguist. And when Spike Jonze finally reversed the footage and played it forward with the proper version of the song, well, The Pharcyde was walking towards us, but there were group members with clothes flying back onto them, basketballs bouncing up flights of stairs, water shooting up into the sky, and many more puzzling, reversed images that made us wonder, "Is this real life?" It wasn't iconic like some of the other videos on this list, but what it didn't make up for in image-driven legacy, it does for the fact that it brought an unprecedented level of sheer, balls-out creativity to the music video-making process that it'd be a harbringer for in the future.