Unless you recognize the character from the title, please tell me what you think this picture is meant to portray. Given the information I've provided, what do you know about this guy? Rest assured, I will lay all my cards on the table eventually but for now I want to hear what your first reaction is...

Third verse same as the first
If the background isn't black, then the image is sure to lack
You should view it in context 'cos that's the way it looks best

alx:

Third verse same as the first
If the background isn't black, then the image is sure to lack
You should view it in context 'cos that's the way it looks best

The backdrop on which you displayed
makes the viewer a little dismayed
You posted it here
against a light backdrop I fear
so it's up to you to fix how it's made.

Well, I thought it was an old woman at first. He has an elegant face and long hair, and in real life men like that could be mistaken as a woman, too, so I don't think that is a problem.

Composition wise, his head is right at the middle of the canvas. I think it will look better if you move it up more.

Like most of your images, there is a hint of light but the lack of contrast suggest ambient lighting. Usually, if it is a strong light from a single ambient light source, it lights up the room quit evenly. If it is a small amount of ambient light, then it will light up only the object around it, so your character should be almost invisible, which probably isn't idea, and if it is a spot light, you should have stronger contrast.

Also, the light area of his chin and the light area of his forehead is a little too close in values. If you want to show the form of the head better, you might want to adjust the values.

I really don't think it would matter if it is viewed against bright or dark background. I think most people can look at an image as the way it is. If you insist, then it might help to add some very thick black border yourself. But if the image is solid, which I think it is, then whatever beyond this picture shouldn't matter.

 Hopefully I've resolved most of the lighting issues, and butched the guy up a bit. How does it look now?

I think this is definitely heading the right direction. The lighting looks nice now, but there are a few obvious inaccuracies that makes it less convincing, mostly details. For example, his eyebrows have the same value on both side. While the local color of eyebrows are supposed to be dark, Some area should still be slightly lighter when light is hitting on it, especially when the skin between the strands are lit by the light.  Also, his eyes don't have any structure; the right side of his face is being hit by the light, so the light should run from his forehead to the cheek, which means the eyelid on that side should catch some light, too. His nose would probably catch some light, too. Finally, some shadow on his face should have hard edge, like the cast shadow from the nose.

This is why I wish folks would audit my work on a black background- the eyebrows actually did have different values but shrunk down on a lighter, warmer background the difference disappeared. Not a big deal since they did benefit from the rework (they looked kinda bolted on before) but also the background here makes his hair look kinda blue which also made him look fem. Check this link out to see the difference http://www.bigskyhorizons.com/alx/gallery/port/1.htm (The same file on a black background)

While his eyes are meant to be enshadowed to indicate brooding and anguish, I've picked out a few details which hopefully satisfy the demands of lighting while still keeping that dark sunken vibe

Regarding the hard nose shadow: I knew it needed one but I don't know how to paint those yet, nor do I have any reference for that. Good call but I'm not cool enough to pull it off today. Here's my best shot but I think we all agree that it doesn't get the job done...

Well, that's all I have to say about this piece other than xie xie to Yian for his patient support and that for the near future I will attempt to work more from photographs and try to learn to paint hard shadows

Today's experiment........... FAILED! It looks alright but not the way I wanted it to

Hey alx, it is difficult to provide feedback if you keep bringing up the black background issue. Could we just settle this? Black background makes no difference. Your work should look good with or without black background. I have never heard any other artists make something that is not part of the painting such a big issue.

And about the nose shadow, I think it looks rather nice in your attempt. The nose really looks like it has form and volume. If you could apply this treatment to other areas that should have similar value and similar edges, like his upper lip and the transition of planes between his brows and eye socket, it will definitely look better. A lot of your piece has very soft shadow everywhere, but no hard edge shadows, so the forms don't feel very successful. This nose look much nice in comparison.