Somehow I think FOV starts coming into play here.
Making her head taller simply doesn’t look right.
So I’m sticking to perspective view a lot more for the last bit.
Yes I'm pretty sure ortho views create distortions when working over a photo.
So note to self -- Heads are not as tall in perspective as in ortographic view.
There probably are other differences too.
Maybe the chin should be higher too? Anyone else welcome to comment.
Hey Spin99, one thing that helps A LOT are the basic proportions of the human head. It’s almost the same for any person, for example, the eyes have to be exactly in the middle of the head and the head is five eyes wide (check all this in the ortho view)
This way you get the correct size for the head. Also don’t forget that even if the wireframe is over the photo and everything seems to match, it’s often misleading for lots of reasons, like incorrect FOV, incorrect alignment of the model, asymmetry, quality of the references etc
@ Fabio Doná Thanks for the comment.
Yes I agree on proportions and the FOV dilemma.
On my current viewport and in perspective the head really looks fine.
Eye spacing is according to reference where to me it seems Madonna
has very slightly closer eyes than one eye spacing between them.
But I really haven’t presented them finished yet.
The reason I haven’t moved the scalp up is that it simply starts looking wrong.
I definitely tried. Also the chin seems to look right with a slight adjustment.
So I’m looking at the perspective viewport and doing minor changes as needed.
I guess it depends a little on how you measure.
With lids the 5 eye theory is totally off to me. I never liked it.
But I suppose you could count five eyeballs in there and then it would be true again.
Endless debate lol. I’ve always preferred looking at eyes + lids to measure proportion.
nice so far - the only thing bothering me is the back of the head - starting at the ears - it’s very narrow there, where the real head’s quite substantial [look at a skull]. Other than that - shapes please 
Thanks Madgalena.
I wonder if it’s that far off? I dunno viewport drives me nuts sometimes lol
I’ve been hoping to be off the hook until next Monday to start 15 days at an expression a day. And have been planning to use not this brushed head but a retopoed lower poly one.
With a rig? LOL
Then I can have lower poly expressions that I can animate in XSI and paint displacement on individually. Tell me it’s wrong and I’ll drop it.
If it sounds too ambitious then maybe I’m happy with only doing a couple of expressions.
Then I can pick my favourite and do Madonna’s portrait? With hair?
And have animatable Madonna I can work on further? Dunno that was my plan 
I worked on her eyes.
Still trying to keep a slight cartoony look.
Hopefully she’s about done?
You have to measure it directly on the model, or with photos with very little perspective distortion. The eyes appear bigger in perspective, so the head will look narrower. But if you use a photo with less distortion you can see the head is actually wider.
@ Fabio Doná Thanks a lot for the reference.
Yes just the outer 2 eyes as you can see are always less than the others lol
To me they don’t count as “eyes” maybe smaller eyes?
Hoping she’s not too far out, really can’t spend a lot longer on modeling.
And she doesn’t have a throat yet AND I’m off tomorrow.
Ok I’ll have the panic attack later tonight.
UPDATE Maybe she needs a bit more cheeks?
Please notice I’m simplifying her eyes for a clean “cartoony” look.
UPDATE UPDATE Yes just a little more volume on the side of the head perhaps.
Haha don’t sweat it too much, we’re all in the same boat 
Having said that, I had my panic attack earlier, on the weekend. “Hardcore” is the word…
That’s because it’s only really 5 eyes without any perspective, so in orthographic view it would be at least 5. in perspective it always seems a little narrower. That’s why I tried with another photo, with a little less distortion, also note that the head in that picture is slightly rotated. Anyway, I hope that helps.
@ Fabio Doná Yes I checked again and changed things a little.
It doesn’t seem to be a bad match? Yes I stylised her chin and eyes.
The idea was to beautify a little. Hope it’s not too bad.
Maybe you can see it better on next update
@ Intervain Looked at the back of her head and it’s so true I always forget
how long most people’s heads are at the back. Maybe it’s a genetic problem.
Any case a bit of skull loving later hopefully better now…
I think her jaw is too wide, you have to make the head an oval shape in the front view, the widest point being a little above the eyes, and the jaw line will be the narrower part of this oval outline.
You can push the ear and the neck further back
I think the shape of the head is a bit better now. I’ve been concentrating on the features a lot without a side view of the skull and that’s what happened.
I like to think the wide jaw goes with the simplified eyes but maybe you don’t like it?
The rest I’ll comment a bit later have to be off today.
Thanks for the very clear insightful comment. It’s helping
Wow, this is realy great. I got no crits cept, shes got one of those heads that is so odd, that its easy to mistake the work for caricature. I think your model is almost spot on.
@ Airflow Thank you Airflow! Very nice to hear.
@ stridiggio Thanks stridiggio yours has been looking like it needs a bit of work.
I think you need to look more at the volumes of the face,
also remember that teeth always come together in an arch, like a horseshoe.
And she’ll get just a little more work still.
I think I’m not getting a weekend.
Want to at least have something to rig next week.
And I’ll be behind the deadline.
Yes the head looks better now 
I must be honest though and tell you that I don’t really like the style/form of the features, especially the jaw and the cheeks. But this is just me. I want the comments to be helpful, so don’t worry about that.
I want to look at the cheeks a bit more not sure if I’ll change the chin much.
As they say, you can’t please them all? Back to work soon
And so she drops her jaw. Could it be singing?
Yes she doesn’t have a throat yet which may look a bit uncanny.
Any case moving along.