[7] After graduating, Gregory began teaching acting classes and directing several productions at East Chicago Central High School and Indiana University Northwest.
He remained in the cast for two and a half years, then moved on to originate and star in other principal roles on Broadway including Tarzan (Terk), Cry-Baby (Dupree), Sister Act (Eddie Souther) and Motown: The Musical (Berry Gordy).
He has also appeared on The Daily Show (Comedy Central), The View (ABC) and David Tutera’s CELEBrations with Kym Whitley.
Current/Future Work In the spring of 2013, Gregory created, produced and starred in the one-man show, The Eve of Jackie,[9] which premiered in New York to sold out audiences at 54 Below and at Chicago's Black Ensemble Theatre.
That same year he received his honorary doctorate degree from his alma mater, Columbia College,[11] and had the honor of giving the commencement address.
He has released several albums and worked with music legends such as Phil Collins, Marc Shaiman, Henry Krieger and Artie Butler.
Other collaborations include Ledisi, Keyon Harrold, Dot Da Genius, MaliMusic, 88-Keys, 9th Wonder, The Pocket Queen, Cory Henry, and Chance The Rapper.