I don't mean any offense but Henry always seemed to give off the "crazy" aura. You know, kind of psycho but in a good fun way. I love characters who show immense personality and craziness(Examples are Kefka from Final Fantasy VI and Dimentio from Super Paper Mario). Well done this is flawless I like this piece a lot!
I think he would have looked even better if he were smoking a cigarette (doesn't he smoke? I mean, I kinda stalked your gallery once and saw him smoking in a few pics.). That would really add to the b/w effect. Maybe even an old 1940's era city road behind him at night (either during rainfall or just after rainfall) with the lights being reflected in puddles on the street, and people walking by and taking quick glances at the one guy in the whole city not wearing a trench coat and hat. And maybe even a sign hanging over a door into an old speakeasy...I think it'd be interesting to see a modern-day character in a 1940's setting and atmosphere.