Page 2 #3. Not too fond of the shirt on the last page…though it may make you stand out…
I don’t know headshots from hamsters, but given the fact that (like Jack Black fpr example) you’re kind of an average looking guy, and not model/movie star “pretty”, shouldn’t your head shots be more oriented toward more of a “character actor” type portfolio with less typical “cheesecake” shots, and more action shots of you in various emotional modes?
What kind of head shots does/did Jack Black use to get work?
First off let me say that I dont’ think it is a very strong group of pictures.
I would not use anything from from group 1 or group 2.
If I had to use one of these with would either be group 3 C or group 3 E.
Those seem to be the most natural and you are not mugging for the camera. Even if you are basically a comic actor you don’t need a comic headshot.
Finally I would ask some DIRECTORS or PEOPEL WHO CAST PEOPLE IN PLAYS which one they like.
Warning!! Warning!!
Answer from a homosexual male!!
Number 2
:eek: :eek: 
Heterosexual male photographer checking in…
My opinion:
Group 1:
a) Decent. I don’t like the shadow area by the lips, though. Plus that stray wisp of hair bugs me.
b) Too squinty, too many wrinkles near your eyes. Smile doesn’t look natural. You look like you’re half smiling, half constipated. 
The chair leg in the background bugs me too. Your left eye is too much in the shadow, too, and this takes away from the impact.
c) Not bad, but makes your face look too full. Not your best angle.
d) Definitely my pick of the bunch. Good lighting. Good expression. No unsightly wrinkles or bad shadow areas. Good eye contact. The whites of your eyes really jump out in this photo. This is the one, no question.
Group 2.
a) Going for that moody lighting from below, eh? If you’re going for the dark, brooding look (which I guess you are), this is the pick of the bunch. Good direct eye contact, good angle for you face. The only comment is that I wish there was a just a touch of light on top of your hair to set it off from the dark background.
b) OK, but not as direct as A. My eye is more drawn to your neck than your face (because of the lighting and the angle.) Almost, but not quite.
c) Awkward pose. You look uncomfortable in this picture. Definitely out.
d) Not bad. The lighting really accentuates the dark circles under your eyes. But it’s pretty direct. Just crop out or photoshop out that white fabric near your left shoulder. It’s the brightest spot in the photo, and a viewer’s eyes are naturally drawn to it.
e) Not my style, but it’s okay in a pensive rockstar snapshot sort of way. Looks like you should be playing with Interpol or something. 
Group 3
This is the toughest bunch for me to pick.
a) Straightforward head shot. OK. Wish a could see a tad more of your right eye, though.
b) It looks like you’re about to punch the photographer in the face.
c) Another typical headshot. OK. Crop in from the right tighter.
d) Ya know…this one has some character to it. It’s not your typical shot, but it has that innocent boy-lost-in-the-supermarket charm about it. And I mean that in a good way.
e) You look uncomfortable and like you’re about to say something.
f) Of the straightforward head shots, you look most natural and comfortable in this one.
g) Not a good angle.
So there you have it. I’d go with 1D, 2A, 3D/F (depending on your purpose.)
1A or 3C.