22. Digital Underground
Years Active: 1987-2008
Key Members: Shock G, Money-B, DJ Fuze, Pee Wee, 2Pac
Elements of Style: Fur coats, African-print pants and shirts, Sunglasses, Humpty Hump's brown nose
Oakland's Digital Underground proclaimed themselves as the "Freaks of the Industry" and the double entendre referred to more than just getting busy in Burger King bathrooms. The crew's look was kind of out there, especially when it came to Shock G's alter-ego, Humpty Hump.
DU's overall aesthetic was a hip-hop homage to Parliament Funkadelic, whom they often sampled for beats. Digital Underground launched the career of a young Tupac Shakur, who started as a dancer before he got the chance to kick a verse on their single "Same Song." Pac mostly refrained from partaking in the group's outre style, favoring baseball jerseys and snapbacks, although there is one pretty incriminating photo of him onstage in a zebra-stripe Speedo and bucket hat. The group's fame peaked with an appearance in the 1991 Dan Aykroyd film Nothing But Trouble, showing off Humpty Hump's crazy style on the big screen, and they broke up altogether in 2008—but their name, and their inimitable style, lives on.