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He was drafted in while attending Southern Illinois University. After being discharged inhe returned to the university but did not receive a degree. He moved to Chicago with a desire to perform comedy professionally. The club failed and landed Gregory in financial hardship. InGregory landed a job as master of ceremonies at the Roberts Show Club. In an interview with The Huffington PostGregory described the history of black comics as limited: Blacks could sing and dance in the white night clubs but weren't allowed to stand flat-footed and talk to white folks, which is what a comic does. Good evening, ladies and gentlemen. I understand there are a good many Southerners in the room tonight.

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