Lol, it does look like he is looking upward and smiling indeed
To me it looks like a guy with a moustache looking upward and smiling showing his teeth. However if you look closely, it might also be that he's not looking upward and that his "teeth" is actually his nose, and his "moustache" are his eyes.
It does look like the guy that is standing 11-12 feet NNW of the well is actually looking at the sky tho. Probably looking at the plane as it flew over