Fresh out of college, Bennett decided that his Math major would be best put to work in science’s most daring field, stand up. Most of the writers of the Simpsons were Math majors, and like them, Bennett can only express emotions through cartoons and one-liners. Bennett co-runs Madison’s Backyard Comedy show. He regularly performs at Madison’s Comedy Club on State and has opened for Noah Gardenswartz, TJ Miller, and Gary Gulman. In 2018 Bennett has been in the Madison comedy festival, Hoboken comedy festival and won this season of Madison’s Big Diss Roast Battle!