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Like so many New Orleans musicians, he settled in Chicago in the early 1920's. He worked with several bands in the city including, Doc Cook's Dreamland Orchestra, Erskine Tate, Ollie Powers and with Charles Elgar Creole Orchestra at the Savoy Ballroom. By the time Jazz became widely recorded Freddie's better days were behind him, but his wild and ragged style is well represented by the song Stock Yard Strut that he recorded with his Jazz Cardinals in 1926. Keppard was an alcoholic, and became an unreliable band member. He continued to work up until 1928.
Freddie Keppard was an important musican who succended Buddy Bolden as "king" of the cornet players in New Orleans. He started playing around 1906, leading the Olympia Orchestra and playing in marching bands, funerals, and Storyville clubs. He also played with the Eagle Band. In 1912 bass player Bill Johnson asked him to round up a group of musicians and come to Los Angeles with the promise of work. This band became known as the Original Creole Orchestra and from 1912 to 1918 it toured the country in vaudeville shows, giving northern audiences their first taste of authetic New Orleans Jazz.