Notably, O'Brien was pianist, composer, and arranger with the Ted Weems orchestra from 1925 through 1941.
[i] He went on to Muhlenberg College, where he was in a fraternity, and then to Columbia University, where he studied organ with David McK.
In 1940, ASCAP attempted to double its fees to broadcasters for the airing of licensed songs.
For ten months – January 1, 1941, to October 29, 1941 – radio broadcasters, namely NBC and CBS, banned all music licensed by ASCAP.
Given the timing of the launch of "My Greatest Mistake," the ASCAP boycott, according to O'Brien, stunted the momentum of the song's popularity.