In 1940, Eddy began working with Pee Wee King in the Golden West Cowboys. With the group, he made regular appearances on the Grand Ole Opry. Colonel Tom Parker, later Elvis' manager, snapped Eddy up as one of his first clients. Eddy had his own radio program in 1943, and later again in the 1950s. He found himself at the height of his career in the late 1940s. In a period of just 14 months between 1947 and 1949 Eddy had six number one songs.