History best remembers singer Allan DeWitt as the vocalist Tommy Dorsey let go so that he could hire Frank Sinatra. DeWitt, a protege of Andrews Sisters manager Lou Levy, sang and recorded with Tiny Hill’s orchestra in mid-1939 before replacing Jack Leonard in Dorsey’s outﬁt that November after Leonard and Dorsey had split on unamicable terms. Dorsey wasn’t happy with DeWitt, however, and when he learned that he could tempt Sinatra away from Harry James in January 1940, DeWitt was quickly gone. Though he spent less than two months with Dorsey, DeWitt recorded with the band.
After leaving Dorsey, rumors had DeWitt joining Bob Chester. He was with Jan Savitt in July, though, for whom he also recorded. He remained with Savitt until at least October 1941. Beyond that, DeWitt disappeared sufﬁciently enough that Down Beat magazine posted his name in their “Where Is?” column, twice, in November 1942 and March 1944, seeking information on him. After his time with Savitt, he appears to have settled in Chicago, where he remained for the rest of the decade. He resurfaces there in early 1944, singing with Jimmy Jackson’s orchestra. By June he was with Wayne King, only to be drafted shortly thereafter. DeWitt served in the Army, where he was stationed at Camp Lee, Virginia, in September.
DeWitt again disappeared long enough for Down Beat to ask where he was in 1948. The answer was leading his own band in the Midwest. In 1949, he both recorded with that group and later as vocalist with Frankie Master’s orchestra on the small Chicago-based indie label Barthel.
In 1940, DeWitt had a loyal fan among the prisoners at Pontiac Reformatory in Illinois. This particular prisoner used two of his allotted four letters a month to write to the singer. In one letter, the prisoner lamented that his Down Beat subscription had expired, and DeWitt promptly renewed it for him.