The songs of Sleepy John Estes constituted a poetic, personal and insightful body of work that both portrayed and transcended the everyday troubles, hardships, and meager pleasures of life in Brownsville, Tennessee. As Ray Harmon wrote in Rhythm & News, “ . . many have asked what it is that makes John’s music so vital, so absolute in its sense of emptiness and desperation. His voice, filled to the brim by the lackluster existence of life in a poor farming community, informs all that hear it of the barely suppressed passion in his words. . . . John’s music is that of an extraordinary man caught in a mundane world, but captivated by the very things that make this world mundane.” Estes, born Jan. 25, 1899, in Ripley, Tennessee, sang with conviction about his work, travels, friends, and townsfolk, as well as his loves, laments, hopes and desires. He began his recording career with the anthemic “Broken-Hearted, Ragged And Dirty Too” in 1929 for Victor Records. Subsequent sides included the classics “Diving Duck Blues”, “Drop Down Mama,” “Someday Baby” – known in other artists’ variations as “Worried Life Blues” or “Trouble No More.” As Big Bill Broonzy wrote in Big Bill Blues (1955), “We called Sleepy John Estes’ way of playing and singing the blues ‘crying the blues’, because he did really cry when he was singing work songs or some blues.” Broonzy also wrote that Estes was 87 years old then, and many thought him to be dead until Big Joe Williams and Memphis Slim spread the word that he was still in Brownsville. David Blumenthal filmed him there for a documentary and soon John was embarking on a new career, recording for Delmark in Chicago and traveling around the country and overseas, where he was greeted with stirring ovations from audiences who knew nothing of Brownsville but who knew a great blues poet when they heard one. Estes, nicknamed “Sleepy” because of his appearance and a condition that caused him to doze off, lost his sight in the 1940s, and made a song about that too (“Stone Blind”).
Estes, who frequently partnered with Yank Rachell or Hammie Nixon, died in poverty on June 5, 1977, despite his international renown. His house in Brownsville was turned into a museum in 1998.

— Jim O’Neal