Sykes began playing while growing up in Helena. At age 15, he hit the road, developing his rowdy barrelhouse style around the blues-fertile St. Louis area. Sykes began recording in 1929 for OKeh and was signed to four different labels the next year under four different names (he was variously billed as Dobby Bragg, Willie Kelly, and Easy Papa Johnson)! Sykes joined Decca Records in 1935, where his popularity blossomed.