He studied with Sanford A. Moeller and began playing professionally in the mid 1920s with bands in Wisconsin. He broke into the Chicago scene in 1927, when he was picked by MCA to become a member of "Thelma Terry and Her Playboys," the first notable American Jazz band (outside of all-girl bands) to be led by a female musician. The Playboys were the house band at The Golden Pumpkin nightclub in Chicago and also toured extensively throughout the eastern and central United States. Krupa made his first recordings in 1927, with a band under the leadership of banjoist Eddie Condon and Red McKenzie: along with other recordings beginning in 1924 by musicians known in the "Chicago" scene such as Bix Beiderbecke, these sides are examples of "Chicago Style" jazz. The numbers recorded at that session were: "China Boy", "Sugar", "Nobody's Sweetheart" and "Liza". The McKenzie - Condon sides are also notable for being some of the early examples of the use of a full drum kit on recordings. Eddie Condon describes what happened in the Okeh Records studio on that day (in 'We Called It Music' - pub: Peter Davis, 1948...
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