"School Spirit Skits" – Kanye West and DeRay Davis
Kanye West hooked up with fellow Chicogoan and funnyman DeRay Davis for his 2004 debut album, College Dropout. The modern-day Mozart also reunited with Davis on his Late Registration album. Davis delivered a spot-on impersonation of the late Bernie Mac on "Wake Up Mr. West."
(Photos from left: PacificCoastNews.com, Christopher Polk/Getty Images)