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I think it’s because the head appears to be more spherical, whereas human heads are more of an egg-shape. It probably doesn’t help that the ear sizes appear to be inconsistent and the nose unsuitable for hominid-shaped faces. The next is more of a personal nitpick, but it looks unsettling to have Applejack looking away from the ‘viewer’ when this is clearly an artistic setting for either a photo shoot or to have a painting/portraiture done.
That head, it… It bothers me. It is way too big for the body and seems so weirdly portioned. That along with the general style and feel of the paint makes me feel that any second now the eyes will look at me.
I like it.