Patt --
If you're still working on this, I might suggest a few areas to look at, some of which could be contributing to the "angry" appearance. It's a little difficult to "see into" the dark reference photograph, so I may be misreading some areas myself. It's smorgasbord, just take what you like. I do think it's an interesting tonal treatment of the subject, and it seems fitting based on the character descriptions you've given of this fellow.
-- I agree that the slant to the eyes is a problem. In the photo, I see the inside and outside corners of the eyes as being almost level. I also think the whites of the eyes are too light, so that the contrast with the very dark iris and eyelash areas is quite severe and creates a harsher look than I see in the photo. Also, the brow area between the eyebrows should be darker as the plane of the brow turns under and proceeds to the bridge of the nose. Darkening that area will also reduce the contrast between those kind of "scowly" creases in his brow and the surrounding skin.
-- I also agree that the mouth area could be adjusted just a bit, with substantial benefit. Starting with the top edge of the top lip as it moves to our left, you've got an arc running from close to the center of the mouth all the way out to the corner and beyond, whereas in the photo, something different is happening. About two thirds of the way to the corner of the mouth, the top edge of the lip actually stops dropping and almost levels out some distance from the bottom lip, and it doesn't proceed to a sharply defined intersection at the corner. While hardly indicating mirth, that little nuance alleviates the pulled down look that suggests displeasure. I also think your highlight on the bottom lip is too light. Finally, it seems to me that the light on the upper lip (I mean the area between the mouth and the nose) is too bright and furthermore, its shape suggests a concave form that is pushing the top lip of the mouth outward, whereas it appears from the photo that the upper lip, rather than being concave, is rather full and round and flows smoothly down and around the top lip of the mouth.
-- One other thing that I think is contributing to the "severity" of the expression is the chin. It seems a bit lopsided, for one thing, almost suggesting a clenched jaw, and it may be just a bit large, so lopping off a bit from the bottom to level it would help in both regards. Then there's the reflected light, which doesn't seem to me to belong there at all and which is giving the chin a sharp-edged look that doesn't appear to be supported by the photo. Rather than getting lighter at the bottom edge, it should be getting darker as the plane of the face turns away from the light. (I realize the reflected light has to do with the shirt, but that tiny bit of exposed collar wouldn't, I don't think, generate perceptible reflected light at all, much less one nearly as bright in tone as the shirt itself.)
Working on those three areas just a little may take care of your client's concerns about the portrait "expression".
A comment about the matter of light and shadow. You've got some very form-descriptive shadow areas in both the face (and neck) and the hands in the photograph, but you've largely omitted them from your painting. Indeed, what is the shadow side of the face in the photo is in fact about the lightest flesh tone in your painting. I think I would have taken greater advantage of those shadow shapes, both for that form-creating purpose, and also so that you did not find yourself having to "imagine" contours and light effects that couldn't actually be seen in the photo.
One final item -- you've done quite well with a very difficult drawing challenge, the interlaced fingers. One thing you might consider revising is the ring finger on his right hand, which in your painting is straight in the last two sections, reaching almost to the edge of the canvas, whereas in the photo it appears that that finger lies down alongside the back of the left hand, as do the other fingers. Also, without shadows in amongst the finger shapes, they're a little more difficult to "read" than would otherwise be the case.
Best wishes,
Steven
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