Complex sentence: Originally performing in minstrel and medicine shows, Jackson was playing all around Chicago in the early 1920s, soon recording "Papa's Lawdy Lawdy Blues" and "Airy Man Blues", the first recordings by a male singer of the blues.
Split into simpler sentences: Originally performing in minstrel and medicine shows, Jackson was playing all around Chicago in the early 1920s. He soon recorded "Papa's Lawdy Lawdy Blues" and "Airy Man Blues", the first recordings by a male singer of the blues.