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.
After that boy, did they deliver. Here are some of the best stories. The footlong wiener. I dated a dude who was packing a footlong. The sex was uncomfortable, at best, after that he refused to go down arrange me. I dumped him after a year of making up excuses en route for not have sex. The crazy amount was that he had no evidence that he was big — all time we talked about his amount, he couldn't believe he was everything more than average.