her mother's annoyance, Calloway dropped out of Morgan College in the early 1920s to seek out a career in music. Family Blanche Calloway's first common-law husband was Henry Waddy; he played multiple roles throughout their relationship, not only as a romantic partner but also functioning as Calloway's manager and agent. They lived and worked together throughout the 1920s and Waddy became close with Cab Calloway as well, who often referred to him as ‘Watty.’ Early professional career Even in her youth, Blanche Calloway was a singer, starting in choir concerts given by the local Grace Presbyterian Church in Baltimore. By 1921, Calloway left home to tour with cabaret troupes, specifically the Smarter Set Co., originally established in 1909 and led by brothers Salem Tutt Whitney and J. Homer Tutt. Calloway appeared in one of the brothers’ skits Up and Down as one of the featured ‘Bronze Beauties’ on December 5, 1921. From there, her roles expanded from chorus girl to bit parts, and eventually to featured singer. Calloway made her professional debut in Baltimore in 1921 with Eubie Blake and Noble Sissle's musical Shuffle Along. Her big break came in 1923 on the national tour for Plantation Days, which featured her idol, Florence Mills. The show ended in 1927 in Chicago, and Calloway decided to stay there, as it was the jazz capital of the world during the time. The club, the Sunset, became her main stage and where Cab Calloway likewise worked after his move to Chicago. Surprising for the time, Blanche Calloway earned higher wages than Cab, making around two to three hundred dollars whereas Cab regularly made $35 a week. She became popular in the Chicago scene and would continue to tour nationally, performing at New York's Ciro Club in the mid-1920s. Shortly after her time at the Ciro Club, she moved to Chicago, Illinois. In 1925, she recorded two blues songs, which would be promoted as race records, accompanied by Louis Armstrong and Richard M. Jones; the first inception of her Joy Boys orchestra. During this decade, she would also perform with Reuben Reeves and record on Vocalion Records. At one point, she performed with her brother's band before going on to work with Andy Kirk's orchestra, the Clouds of Joy, at the Pearl Theater in Philadelphia in 1931 and recorded three songs, including a song she wrote which has been called her "trademark" song: "I