Simon Season 1 Episode 2 Simon Goes on a Date ( Air Date 1995-09-17 ) Genre Comedy category. Overview "Carl, a successful Wall Street stockbroker, loses his job and his wife, and finds himself in Harlem, sharing a tenement apartment with his simple brother Simon. Just as Carl's situation couldn't get any worse, a stroke of luck lands Simon a high-paid position with a cable TV network, forcing Carl to come to terms with his brother's success.".