History best remembers singer Allan DeWitt as the vocalist Tommy Dorsey let go so that he could hire Frank Sinatra. DeWitt sang and recorded with Tiny Hill’s orchestra in mid-1939 before replacing Jack Leonard in Dorsey’s outfit in November 1939 after Leonard and Dorsey had split on unamicable terms, but the new singer wasn’t working out, and Dorsey was looking for someone else. When he learned that he could tempt Sinatra away from Harry James in January 1940, DeWitt was quickly gone. DeWitt did manage to record with Dorsey, however, during his short stay.
Other than his connection to Sinatra, DeWitt is most noted for his work with Jan Savitt’s orchestra in 1941, with whom he also recorded. He worked with Wayne King’s new band in 1945, and in 1949 he both sang with Frankie Master’s orchestra and fronted his own band on the small Chicago-based indie label Barthel, where he recorded four sides.