From 1920 to 1923, he primarily played piano accompaniment for blues singers. Henderson toured with the Black Swan Troubadours featuring Ethel Waters from October 1921 to July 1922. After hearing Louis Armstrong in New Orleans while on tour in April 1922, Henderson sent him an offer, but Armstrong refused because Henderson would not hire Zutty Singleton as well. His activities up to the end of 1923 were mainly recording dates for Black Swan and other labels. His band at this point was only a pick-up unit for recordings, not a regular working band. In January 1924, the recording band became the house band at the Club Alabam at 216 W. Despite many erroneous publications indicating otherwise, this 1924 band was Henderson's first working band. In July 1924, the band began a brief engagement at the Roseland Ballroom. Although only meant to stay for a few months, the band was brought back for the autumn season. Henderson called on the 23-year-old cornetist Louis Armstrong for a second time to join the band. Henderson's offer on Octomade history when the Henderson band began their re-engagement at Roseland with Armstrong now in the orchestra. The band quickly became known as the best African American band in New York. By late 1924, the arrangements by Don Redman were featuring more solo work. Redman arranged Armstrong's repertoire with the King Oliver's Creole Jazz Band, such as turning "Dippermouth Blues" into "Sugar Foot Stomp". Armstrong played in the band for only a year, because he could not grow accustomed to the arrangements and to the "pretension" of the other band members.
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