One of the first inductees into the Alabama Jazz Hall of Fame, Fess Whatley, is a fascinating figure of the time. Black musicians played in White establishments, particularly those serving bootleg alcohol, throughout the period in which this setting takes place. You can find information on Fess Whatley at
https://www.bhamwiki.com/w/Fess_Whatley. Check out bhamwiki.com for all sorts of period research for your game.