I may be having faaar too much fun with this character. Here's some more attempts to narrow him down, and also to start injecting some kind of style. I aiming to inject some kind of vulnerability and craven. I think that the upper middle and lower left do the best job of this. He's a difficult character to capture, everything about his style needs to scream "NOIR DETECTIVE", while his posture and mannerisms tell a different story of delusion and cowardice.