Despite what seems like a rough background as a child, this trumpeter and vocalist was fond enough of his hometown of New Haven, Connecticut, to spend most of his time there, including the final half of his career. Billy Douglas was mostly active on a local basis and within the state of Connecticut except for the period between 1932 and 1945 when his playing found him more often in the limelight, including some recording with the great pianist and bandleader Earl Hines. Douglas' first collaborator of importance was the saxophonist Larry Ringold -- they met and began playing music together when both were housed in a New Haven institution for boys.
From there Douglas began to make a name for himself as a local performer, then went to New York City with a band led by Earle Howard for a year beginning in 1932. Douglas also spread his talents northward, appearing in Boston with Howard as well. From the fall of 1933 through the spring of 1934 he performed in Hartford, Connecticut in Percy Nelson's band, the Night Hawks. Subsequently he went on tour in the South with the well-armed ensemble of Jimmy Gunn and seemed to be developing into the type of hot, in-demand talent hipsters like to describe as "happening." Another bandleader, Don Albert, grabbed Douglas away for the featured soloist spot in his own group -- here was an example of a Gunn not being able to halt a hijacking. This job lasted through 1937, after which Douglas began to freelance. He worked with Hines in the mid-'40s but seemed to go for smaller profile jobs in later years.