[3] There is some speculation Wheatstraw may have been born in Cotton Plant, Arkansas, where he was buried, and blues musician Big Joe Williams stated that this was his hometown.

[4] The earliest biographical facts come from the musicians Henry Townsend and Teddy Darby, who remember Wheatstraw moving to East St. Louis, Illinois,[1] in the late 1920s.

[2] He often performed at a club called Lovejoy in the East St. Louis area and at a juke joint over a barbershop on West Biddle Street.

[5] By the time Sunnyland Slim moved to St. Louis in the early 1930s, Wheatstraw was one of the most popular singers there, with an admired idiosyncratic piano style.

His total output of 161 recorded songs was surpassed by only four prewar blues artists: Tampa Red, Big Bill Broonzy, Lonnie Johnson and Bumble Bee Slim (Amos Easton).

[14] African-American music maintains the tradition of the African "praise song", which tells of the prowess (sexual and other) of the singer.

First-person celebrations of the self provide the impetus for many of Wheatstraw's songs, and he sang changes on this theme with confidence, humour and occasional menace.

"[15] The blues critic Tony Russell updated the description: "Wheatstraw constructed a macho persona that made him the spiritual ancestor of rap artists.

Samuel Charters, in The Country Blues, dismissed Wheatstraw and other recording stars of the period as tending to "a repetitious use of clichés and a monotonous accompaniment that was as unimaginative as their singing".

Much more distinctive was his vocal style, often described as "lazy" because of his loose articulation, but better represented by Tony Russell as "gruff" and "clogged".

Most distinctive of all was his strangled semi-falsetto cry "Ooh, well, well" (with variations) interjected in the break of the third line of a blues verse.

On some of his last dates, Wheatstraw recorded music in a jazz-inspired framework, collaborating with Lil Hardin Armstrong and the trumpeter Jonah Jones.

Perhaps the most obvious example of his impact is in the lyrics and vocal stylings of Robert Johnson, often considered the most important blues figure of the era.

Elements of his style can be seen in later artists, like Champion Jack Dupree, Moon Mullican and Jerry Lee Lewis.

Traveling at a high speed just a block from Wheatstraw's house, the Buick they were riding in struck a standing freight train, throwing all three men from the car.