Born in Tallahassee, Florida, Issac Knight, or Ike as he sometimes known, became a Highwaymen and painter inadvertently. He got his start by being a seller of Alfred Hair and Al Black's paintings. Al Black was his brother in law, and he mentored him in painting. He began working as a painter in 1968 but still maintained his full time job, which would only allow him to paint in the evenings and late into the nights. On weekends, usually on Saturaday, he would go out and sell his paintings. The Jetties In Fort Pierce was one of his favorite selling places. He also took day trips to sell as far north as Tallahassee and south as far as Miami.