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O'Bryant played with the Tennessee Ten in 1920-21, then in a group with Jelly Roll Morton and W.C. Handy in 1923. In 1924 he played with King Oliver. From 1923 to 1926 he recorded extensively with Lovie Austin's Blues Serenaders, and also did sessions with his own Washboard Band. He died in 1928 at the peak of his career. His entire output as a leader was reissued on two compact discs by RST Records in 2000-2001.