In 1929 he makes his first records, for the Victor record label, in Memphis.
John is working regularly in brownsville with hamonica player Hammie Nixon.
He begins recording for the Decca label in 1935 but the association ends in 1940.
The following year after recording for 12 months John's association with the Bluebird record label ends.
After having spent several years recording in Chicago, John moves back to Brownsville in 1942.
Accompanied by Hammie Nixon in 1948, John records some songs for the Ora-Nelle record label, the six years later he records for the Sun record label in Memphis, but those songs do not appear until the 1970's.
In 1961 David Blumenthal, a Chicago photojournalist, visits John on assignment in Brownsville and enthuses about his visit to blues aficionado Bob Koester.
John's first album The Legend of Sleepy John Estes is released on Koester's Delmark record label in 1962 and two years later he play the Newport Folk Festival and visits Europe.
Bob Dylan, at his peak, mentions Sleepy John in the sleevenotes to Bringing It All Back Home in 1965 and sings in John's style on 'From a Buick Six' on Highway 61 revisited.
John guests on Ry Cooder's album Boomer's Story in 1972 and two years later plays concerts in Japan.
He records for the album Beale Street Saturday Night in 1975.
John Adam Estes dies after suffering a stroke on 5 June 1977.