Jones was born in Bowie County, Texas. He was a street busker in the 1920s in San Antonio. He dropped out of school at the age of 13 to support the family farm after his father suffered from illnesses and crops were destroyed. The nickname "Little Hat" was acquired from a construction job in Garland, where Jones wore a hat with part that of the brim torn. He recorded two compositions, "New Two Sixteen Blues" and "Two String Blues", released as a single by Okeh Records on June 15, 1929. That same day, he played guitar on nine tracks by Alger "Texas" Alexander in the Okeh studio. On June 21, Jones recorded four additional songs for Okeh, and on June 14, 1930, he recorded six more. These three sessions represent the majority of Jones's recorded output: ten songs of his own and nine with Texas Alexander. He also has two tracks on Yazoo L-1010 (LP, 1968), "Hurry Blues" and "Rollin from Side to Side", both listed as recorded in 1929. Jones performed at parties, fish fries and juke joints, often in the company of Thomas Shaw, Texas Alexander, and J. T. Smith.
Jones never recorded another song. He resided in Naples, Texas, where he would stay for the rest of his life with his second wife, while working in various jobs. He died in 1981, at the age of 81.
Jones's style is marked by his tendency to start a song at one tempo and then slow down once he began to sing. Once a forgotten obscurity, he became better known later in the 20th century as historians began to explore the Okeh Records catalogue. His posthumous fame was also boosted by the use of his song "Bye Bye Baby Blues" in the movie Ghost World in 2001.