Emerging from Roseland in Chicago, he attended Thornridge High School before earning an acting degree at Philander Smith College, a foundation that led to a comedy debut sparked by a $50 bet to take the stage. His writing tenure on The Tonight Show with Conan O’Brien (2009-10) and Conan (2010-12) garnered two Primetime Emmy nominations and three Writers Guild of America nods, while his on-screen b…