I saw this and thought "Looks like Baron Samedi!" then noticed the title and my hopes kinda dropped... then read you mentioned Live and Let Die and grinned widely. I find it pretty cool you made a D&D NPC based off of him (which is what I'm inferring from your replies to previous comments).
Time for a joke because laughter's the best medicine. You must be sad because you're somehow related to the girl who made that annoying "Friday" song, and there is no cure for it. *ba-dum-tish* Still frowning because it isn't funny? Oh well. :(
Anyhow, the details in this piece compliment its mood: from the frayed clothing to the frown on his face to the bleak background color, they all work together to make him truly, truly sad. It didn't actually make me sad, but I felt sympathetic for the poor guy. Those eyes though... They make the whole thing come together. You just can't help but stare into them when you look at this piece. The only thing I could think of that would have made it any bleaker would be a fly or two to symbolize death coming from the corpses I'm sure are lying around. Great piece altogether and I'm sorry if I jumped around too much!