Heading into the 90s, hip-hop and urban culture was on the verge of a new frontier.

With the music, fashion, and lingo bred by hip-hop beginning to infiltrate pop culture, new cultural institutions began to emerge, one of them being the legendary comedy sketch show In Living Color.

Created by actor, comedian, and filmmaker Keenen Ivory Wayans, In Living Color would revolutionize the world of sketch comedy by showcasing the marriage between comedy and hip-hop during the show's five-season run.

Debuting on April 15, 1990, In Living Color quickly became one of the hottest shows on television in large part due to its cast of talent, which included an unknown Jim Carrey, Damon Wayans, Jamie Foxx, Tommy Davidson, and a host of other stars that would become legends within the comedy world.

However, in addition to the humorous antics and characters associated with the show, one aspect that drew viewers to In Living Color was its implementation of guest performers, which began during its second season.

Beginning with Queen Latifah, the show's first official rap act to rock the crowd, In Living Color would welcome a diverse cast of the genre's biggest names. Among those that would appear on the show were 3rd Bass, KRS-One, Big Daddy Kane, A Tribe Called Quest, MC Lyte and other premier artists, helping make In Living Color a hotbed for hip-hop and further introducing the culture to middle America by bringing it into prime-time.

We've compiled a list of 15 of the hottest live performances in In Living Color history in celebration of the show's ties to hip-hop.