 He gained attention working with Bob Crosby (1937–1940), and later performed with Artie Shaw, Les Brown, and Benny Goodman.While with Bob Crosby, he initially played third trumpet behind the legendary Charlie Spivak and Yank Lawson.When those two left Crosby to join Tommy Dorsey's band in 1938, Butterfield was given the opportunity to solo on a song written by Crosby bassist Bob Haggart, initially titled "I'm Free."