Circa 1947, he won a Jackson talent show and was awarded a role in the musical short film #The Jackson Jive for his efforts; he nevertheless settled in New Orleans in 1952, and via longtime friend Fats Domino he was introduced to RB great Dave Bartholomew, who helped Webb land a deal with Imperial Records. The following year, he issued his recorded debut, Bad Dog, an archetypal slab of country boogie that found few takers in the face of growing listener demand for more urbanized RB. A frustrated Webb left New Orleans for Chicago, where he spent the next five years toiling in a series of factory jobs. He continued playing guitar at house parties, however, and thanks to the influence of Windy City bluesmen like Muddy Waters, he was an even more original musician by the time he returned to the Crescent City in 1959.
While working by day as a longshoreman, Webb gigged only infrequently, but in 1968 he recorded several songs for folklorist David Evans later issued on the Arhoolie LP Roosevelt Holts and His Friends. The album proved a major favorite among European blues enthusiasts, several of whom even traveled to New Orleans to meet Webb in person. After multiple invitations to tour Europe, he finally accepted an offer to play the 1982 Dutch Utreck Festival. In 1989, thanks to funding from the Louisiana Endowment for the Humanities, he also issued his first full-length LP, the Flying Fish release Drinkin' and Stinkin', but he died on August 22, 1990, at the age of 66. ~ Jason Ankeny, Rovi