Fiddler Henry Clay Gilliland was born in Jasper County, Missouri, on March 11, 1845. He was the son of Joseph C. and Lucretia K. Gilliland. With Alexander (Eck) Robertson, he made the first country music recording in 1922.
Gilliland had immigrated to Texas with his family in 1853. The Gilliland brothers were noted fiddle players in the frontier region near Weatherford, and Henry learned to play on his older brother's (Joseph's) fiddle. Gilliland enlisted in 1863 in the Second Texas Cavalry, Arizona Brigade, and remained in the Confederate service throughout the Civil War, seeing action in South Texas and during the Red River Campaign. After the war he developed a reputation as an Indian fighter and held numerous public offices in Texas and Oklahoma. He was also active in the affairs of various Confederate veterans' organizations, eventually attaining the rank of lieutenant general in the United Confederate Veterans. He married Susie Borden on December 9, 1869, and they had six children. He was elected district clerk of Parker County in 1888.
Gilliland won many many fiddle contests in North Texas during the late nineteenth and early twentieth centuries. He was a driving force behind the organization of the Old Fiddlers' Association of Texas (1901) and served for many years as its secretary. He deftly combined Confederate veterans' issues with fiddle contests and used the contests as a means to disseminate "Lost Cause" ideology. In 1910 Gilliland performed at the opening of the State Fair of Texas. The following year he tied for the title of world's championship fiddler at a contest held in Little Rock, Arkansas. Along with Jesse Roberts and the legendary Matt Brown, Gilliland toured northeastern Texas in a fiddling exhibition shortly after the championship contest.
After the death of his first wife, he married Mrs. Mary Self on August 20, 1914. In 1922 he attended the United Confederate Veterans' reunion in Richmond, Virginia. After the convention he and Eck Robertson journeyed to the New York studio of Victor Records and recorded two sides, "Arkansas Traveler" and "Turkey in the Straw." The session resulted in the first recordings of what came to be called country music. Upon Gilliland's death, in Altus, Oklahoma, on April 21, 1924, the magazine Confederate Veteran memorialized him as "the greatest fiddler of the world."