When I lost my rifle, the Army charged me 85 dollars. That is why in the Navy the Captain goes down with the ship.

Until then Gregory had worked mostly at small clubs with predominantly black audiences. Gregory drew on current events especially racial issues for much of his material: "Segregation is not all bad. Career
After completing military service Gregory performed as a comedian in small primarily black-patronized nightclubs while working for the United States Postal Service during the daytime.

Richard Claxton "Dick" Gregory (born October 12 1932) is an American comedian social activist social critic writer and entrepreneur. Gregory is an influential American comic who has used his performance skills to convey to both white and black audiences his political message on civil rights. His social satire helped change the way European-Americans perceived African-American comedians since he first performed in public.