ALL IN THE FAMILY

(do yourself a favor and click to enlarge.)

First, I'll give you a moment to silently marvel.

There.

You've just experienced a one-of-a-kind work of art which was made up of carefully arranged oil paint on a single canvas. This visual feast was generously imparted to me by dearest Anthony, presumably because I recently revealed that it was the inspiration behind my series of cult film-inspired family portraits.
Painted by the mysterious "Kevin Henry," the piece left the clutches of its original linage by way of an estate sale, then it passed through a yard sale where my wife noticed it and Anthony acquired it.

Here's how this painting works: first, the horn rimmed glasses and large knotted tie invite you in, perhaps even coaxing a chuckle before your eyes meet the uncomfortable gaze of the red headed fellow– a man who's only suitable descriptor is "dapper." Once your eyes meet, his half-smirk turns cold and his face begins to radiate disappointment and a sense of uneasiness. Suddenly you notice that he's waxy, flat, and lacking the definition demonstrated in the other subjects, and his presence takes on a ghostly quality.

My theory? Dapper man is the artist. He was unable to offer as much attention to himself just as his father (theoretically on the right) neglected him all of his life. His dad is obviously a stern man; scrutiny pours from his sneer, and confidence from his pin stripe mustache (or maybe that's just a shadow). Who could live up to his standards with his rigid chin and conquered hair?

Ok, maybe you disagree. Maybe the inconsistency is simply because the image was cobbled together from two or three different photo references. Boooring.
Well if you've got it all so figured out then I've got a whole list of questions for you.... How, specifically, are they all related? Who is Kevin Henry? Why are the outer two wearing black while the middle two seem color coordinated? What is that lapel pin? Is the older lady's eye actually disfigured?

Thanks Anthony, for the many mysteries.