Robert Lee Hill was born in Dermott, Chicot County, Arkansas. Records of Hill's birth and early life are a mystery. Documents with his handwriting seem to show that he had some form of limited formal education. Hill did complete a correspondence course as a private investigator and was known to refer to himself as "Robert Hill, U.S. Detective".
Sometime before 1918 Hill moved from his birthplace to the town of Winchester, Arkansas in Drew County. Hill was married, had two children, and worked for the Valley Planting Company.
While living in Winchester he became active in organizing the African-American laborers and sharecroppers and formed the Progressive Farmers and Household Union of America. Hill based his association on black fraternal organizations, the international trade union movement, and Booker T. Washington's National Negro Business League. Hill intended to use the organization to force landowners to pay tenant farmers their full shares and establish union-owned farms.
During the summer of 1919 Hill encouraged hundreds of African-American sharecroppers and sawmill workers to join his organization. Hill had particularly success amongst African-American veterans of World War I who were embittered over their post-war treatment. During that summer, Hill organized union chapters in the small towns of Hoop Spur, Ratio, Elaine, Old Town, Countiss, Ferguson, and Mellwood.
In the fall, two of the chapters hired lawyers from Little Rock to try and force fair treatment in the courts. Black informants reported this information to local whites. Gunfire broke out at a meeting of the Hoop Spur chapter which led to the famous Elaine Race Riot.
Hill himself escaped the ensuing chaos and fled to Kansas. Hill became the most wanted man in Arkansas and authorities portrayed him as the leader of a conspiracy to kill plantation owners.
On 20 January 1920 Hill was arrested in Kansas after Arkansas police pinpointed his location from an intercepted letter that Hill had written to his wife. After his capture Arkansas officials charged him with murder and asked for his extradition. Federal authorities indicted Hill for inciting to riot and impersonating a federal officer.
Governor Henry J. Allen of Kansas refused to extradite Hill, after intense lobbying by the National Association for the Advancement of Colored People, citing his belief that Hill could not receive a fair trial in Arkansas and would not be safe in Arkansas jails. Hill was released on 11 October 1920 after federal charges were dropped due to NAACP lobbying with authorities in Washington.
Hill fused music, religious imagery, and patriotism into his organizing efforts which leads many critics to label him as a demagogue. There were also unsubstantiated claim that Hill organized the union solely for his own economic benefit. Hill, in a letter, denied any attempt to kill white plantation owners stating that it would be senseless to kill plantation owners in Phillips County, Arkansas when he had local chapters in "25 to 30 counties".
It is known that Hill suffered an injury while working at a packing plant in Topeka, Kansas in 1921. Hill was unable to work and attempted to convince the NAACP to give him a position with that organization. James Weldon Johnson, the NAACP secretary recommended that he join the Topeka branch. No further word of Hill was ever received and his later life has been lost to history.