He got his start in comedy while in the U.S. Army. He entered and won several Army talent shows. After completing the service, he continued performing in small and mostly black nightclubs. He worked for the Postal Service during the daytime. Hugh Hefner hired him to work at the Chicago Playboy Club after Hefner heard him in 1961.
He began appearing nationally and on television and became more involved in the struggles for civil rights and activism against America's involvement in the Vietnam War. Gregory and his wife Lillian, whom he married in the 1960s, have twelve children and reside in Massachusetts.
First Day Cover in excellent condition , dated July 20, 1978, celebrating America's Viking Mission to Mars, boldly signed by Dick Gregory in red ink.