Gene Krupa in Chicago. Bartłomiej was an immigrant from Poland. Anna was born in Shamokin, Pennsylvania and was also of Polish descent. His parents were Roman Catholics who groomed him for the priesthood. He spent his grammar school days at parochial schools. After graduation he attended Saint Joseph's College for a year but decided the priesthood was not his vocation. Krupa studied with Sanford A. Moeller and began playing drums professionally in the mid-1920s with bands in Wisconsin. In 1927 he was hired by MCA to become a member of Thelma Terry and Her Playboys, the first notable American jazz band—all-girl bands
Gene Krupa excepted—to be led by a female musician. The Playboys were the house band at The Golden Pumpkin nightclub in Chicago and toured throughout the eastern and central United States. Krupa made his first recordings in 1927 with a band under the leadership of Red McKenzie and guitarist Eddie Condon. Along with other recordings by musicians from the Chicago jazz scene, such as Bix Beiderbecke, these recordings are examples of Chicago style jazz. Krupa's influences during this time included Father Ildefonse Rapp and Roy Knapp (both teachers of Gene), and drummers Tubby Hall, Zutty Singleton and Baby Dodds. Press rolls were