It all started when Kanye West called DeRay Davis to rap for him on the phone for 8 minutes straight. Both of the stars are from Chicago, and at the time Mr. West was about to sign his record deal, the now-comic was also about to get a music deal. When the recording sessions for ‘College Dropout’ began, the two went to the studio and Ye ended up asking Davis if he wanted to do some skits for the project. It was slow-going at first, and then DeRay started to do an impression of Bernie Mac, who Kanye and his team originally wanted for the album skits but couldn’t lock down.
Though he explains that he had never done the impersonation before and actually hated comedians who did impressions, those very impressions are what ended up tying the entire album together. The skits didn’t stop at the recording booth, either, DeRay actually toured with Kanye for a couple dates, and then ended up being on his following album as well (Late Registration, even though they say Graduation in the interview). All of the skits for that project were improvised, and that ended up sending him to the Grammys with Kanye.
Peep the whole interview on Desus & Mero below to hear the whole story for yourself.
And if you’ve never heard the famous skits from Kanye’s College Dropout and Late Registration….honestly, what are you doing with your life? But just in case you’ve missed it all these years and wanna catch up, take a listen to one of the most beloved skits below.