Before Kanye West started designing for adidas he had plans to start a Comedy Central show with friend and collaborator Rhymefest. They filmed a pilot for the show, titled Alligator Boots, but not much information about the show was known. Today, more footage appears from that episode as well as some more background history surrounding it.
During the 2000s, interest in having puppets on TV peaked with shows like Crank Yankers and the film Team America: World Police. According to a short oral history conducted by Wired, video director and animator Konee Rok revealed that Rhymefest would play this character Pork Troy in the studio during the sessions for Kanye’s Graduation, causing everyone to break out laughing. Kanye then had the idea to bring it to Jimmy Kimmel and his production company Jackhole Industries. Jackhole was responsible for Crank Yankers, among other shows.
From there, Kanye came up with the title Alligator Boots because growing up, having an uncle own a pair of them meant that he had made it, and working on this show felt like that for him. The executive producers for the show would be Kanye West, Daniel Kellison (Jackhole) and Rhymefest. The people who were a part of the show said Kanye was very invested in the wardrobe for the puppets, even considering KAWS to design the puppets at one point.
Another interesting fact is that Kim Kardashian and Kanye first met because of the show. Kanye insisted on having Kim on the show, despite the sex tape with Ray J that just came out at the time.
They shot the pilot with a $1 million budget and five days on the Jim Henson lot. The format for the show included a puppet audience, a live person hosting (Kanye was the host for the pilot), skits with puppets and also moments behind the scenes on set for the puppets. Although it never got picked up, Konee has uploaded a BTS video for the pilot to give you an idea of what could have been. You can see it below.