Akers came to Hernando, Mississippi, a small town near Memphis, Tennessee, as a young teenager, already playing guitar at the time.

In Hernando he met Frank Stokes, who is now often considered the "father of Memphis blues"; together with him he performed as a songster (a form of itinerant musician), comedian and dancer in the Doc Watts and his Spoan's Linament Medicine Show, which toured the southern United States, in the mid to late 1910s.

Both played the Stella brand of guitars, common among blues guitarists at the time, and performed on weekends in the Hernando area, where they made it to local prominence.

[5] "The Cottonfield Blues" was Akers' trademark tune, which he had practiced continually on his own as well as with Callicott since about 1926/27; the recording accordingly clearly illustrates how well the Akers/Callicott team was attuned to each other.

[6] Also, at this session, Callicott recorded his only contemporary release as a soloist, "Travelling Mama Blues", for which Akers is credited as the author.

With the latter, Nate Armstrong, Little Buddy Doyle, and Robert Lockwood Jr. he often played weekends on Beale Street and performed around Memphis in juke joints.

Robert Wilkins reported that the distinctive and, for the time, very unusual rhythm was not necessarily invented by Akers himself, however, but had already been played by two brothers named Byrd in the Hernando area between 1915 and 1920.

This and the bluesy vocal line, which heavily veils the blue notes in intonation and thus distances itself harmonically from the guitars, creates an effect aimed at making the singing, i.e. the singer or narrator, seem left alone, thus heightening the dramaturgy of the textual content (about a man has been abandoned by his lover).

"[10] Musicologist Ted Gioia described his style by saying "Here chord fragments ricochet like bullets off the fretboard, serving as bits of harmonic shrapnel underscoring Akers piercing vocal attack, a long lingering wail that contrasts pleasingly with the rapidfire pulsations of his guitar.".