Big band vocalist Kay Weber was singing in the Donnelly-James Orchestra when she was discovered by Glenn Miller, who was then organizing Smith Ballew's band. When Miller left for the Dorsey Brothers in 1934, he took Kay with him. There she joined Bob Crosby as vocalist. He was soon replaced by Bob Eberly, with whom Kay had a brief romance.
After younger Dorsey brother Tommy left to form his own orchestra, Jimmy began to concentrate on his radio series, on which Kay did not appear. With little left to do in the band she quit in frustration, joining the new group led by her old singing partner, Crosby, where she remained for two years. She married Crosby trombonist Ward Silloway.