Where: Ebet Roberts promotional photo shoot

When: 1980

The Furious Five, along with Grandmaster Flash, is one of the best-dressed crews in hip-hop history. Which is why the photo and outfits above are that much more disappointing. It's no secret that their style eventually grew to be flashy and reflected the rock and disco elements in their music, but this makes no sense at all. The caption in the image probably describes it the best: "Grandmaster Flash and the Furious Five would live to regret firing their stylist."