It All Came True (1940)

Nightclub entertainer Sarah Ryan and songwriter Tommy Taylor move in to the boardinghouse run by their mothers Maggie and Norah. Tommy brings along Mr. Grasselli, a "nervous wreck" who keeps to himself.. Sarah recognizes him as the gangster Chips Maguire. He killed a cop with Tommy's gun, so Tommy must now protect him. Grasselli winds up turning the boarding house into a money-making nightclub.