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Dennis earned a degree in Theatre Arts from Murray State University, where he was nominated for the Irene Ryan Award for his portrayal of The Old Man in Sam Shepard's play "Fool for Love". After graduating, Dennis worked for a time in childrens' theatre, and also worked briefly at the Shadowbox Cabaret near Cincinnati, Ohio. In the summer of 2004, Dennis shifted his artistic attention to long-form improvisation, performing with the Louisville, Kentucky-based group "Project Improv" for a year and a half, as well as working in various independent film and stage productions. Currently, Dennis resides in Chicago, where he is studying at IO (formerly the Improv Olympic) and the Annoyance Theatre.