Mafia III's dev team wanted a cinematic score with a twist. Through an experimental and exploratory demo process, the game's score pointed towards the creation of an interactive, all-original blues score. The blues, however, introduces several challenges: its form and structure is very simple, its instrumentation is limited in color, and often its players, while accomplished, are not musically literate. This talk will address the challenges of working with a music tradition that is not typically used for scoring video games. The talk will address creating concept demos for an alternative ensemble, overcoming scoring and orchestration issues, how to produce efficient recording sessions with alternative methods of communicating with players who improvise or don't read music, how to respect the integrity of a music tradition while stretching its boundaries, and how to technically and creatively work improvisation into a dynamic scoring system.