Gilcrease was born in Robeline, Natchitoches Parish, Louisiana, on February 8, 1890. He was the son of William Lee Gilcrease and Mary "Elizabeth" Vowell Gilcrease, a Muscogee Creek. Mary "Elizabeth" was an enrolled member of the Muscogee (Creek) Nation, and shortly after his birth, the family moved to Indian Territory to take advantage of the allotments in the Creek Nation. The family lived on tribal lands near Eufaula, Oklahoma. After the move, Gilcrease's father ran a cotton gin in the nearby community of Mounds, Oklahoma.