Dale's intention was originally not to be a singer, but to go into journalism. However, he quit school after an argument with a teacher and ended up going from one job to another, until one day in 1943 he and a friend passed by a casino in Coney Island and the friend suggested he try out for a singing job. He was told to come back in the evening, and when he came back prepared to sing two songs, was called back for seven encores. He was immediately hired. In 1944, he joined the Carmen Cavallaro Orchestra as featured vocalist, and at Cavallaro's insistence got a new name. The name was taken from Alan-a-Dale. In 1944 and 1945, Dale sang for George Paxton's Orchestra and became increasingly popular on the East Coast performing at the Roseland Ballroom in New York and recording for Majestic Records.