Estes sang with a distinctive "crying" vocal style. He frequently teamed with more capable musicians, such as Yank Rachell, Hammie Nixon, and the piano player Jab Jones. Estes sounded so much like an old man, even on his early records, that blues revivalists reportedly delayed looking for him because they assumed he would have to be long dead (and because the musician Big Bill Broonzy had written that he was dead). By the time he was tracked down by the blues historians Bob Koester and Samuel Charters in 1962, he was completely blind and living in poverty. He resumed touring with Nixon and recording for Delmark Records. Estes, Nixon and Rachell appeared at the Newport Folk Festival in 1964.
Many of Estes's original songs were based on events in his life or people he knew in his hometown, Brownsville, such as the local lawyer ("Lawyer Clark Blues"), the local auto mechanic ("Vassie Williams' Blues"), or an amorously inclined teenage girl ("Little Laura Blues"). In "Lawyer Clark Blues", about the lawyer and later judge and senator Hugh L. Clarke, whose family lived in Brownsville, Estes sang that Clark let him "off the hook" for an offense. He also dispensed advice on agricultural matters ("Working Man Blues") and chronicled his own attempt to reach a recording studio for a session by hopping a freight train ("Special Agent [Railroad Police Blues]"). His lyrics combined keen observation with an ability to turn an effective phrase.