I'll start with Private Raymond M. Flynn. He was a vaudeville man, and WWI veteran. In 1919 he published the quite serious history book The History of Company E, 308th Infantry (1917 - 1919) [LINK]with Corporal Alexander Hussey. That's Ray on the left in the image above. He was born on February 22nd 1893 so he would have been about 41 years old in that picture. They were sponsored by Rub-ine Liniment. More here.
He was in vaudeville before the war (reputedly) and he returned to it afterward. He tried out a number of different ethnic parodies. But nothing worked until he tried out as half of the duo Joe and Bateese with Harold Crimi, in 1932. Ray played the part of French Canadian Joe LaFlamme. They stayed with the station until 1935. The Variety Radio Directory 1939-1940 still lists the program at WBZ in that time frame, but Flynn describes his own departure in a Lost Battalion bio as 1935 definitively. [SOURCE] That source dates to 1955 when ray would have been at least 60 years old.
A 1934 issue of the Cambridge Sentinel refers to Flynn and Crimi as "local boys" in describing a local theater jubilee they were in. But Flynn at least was really from Holyoke. Close enough. An issue of the Fitchburg Sentinel from the same year describes them appearing at the opening of a film attracting some of their "millions" of listeners. But within a year they parted ways. Crimi vanishes from the record, and Flynn makes it to Hollywood but not to any notable success. In his very short newsletter bio he wrote "My thoughts often go back to the days spent in the "pocket"-days which I am sure none of us who were there will ever forget."