Jensen, DA era, was so pretty-perfect more than one person has referred to the Uncanny Valley effect.

His features are proportionate and regular, but one of his eyes just slightly crosses, there's a small divot out of the right side of the bridge of his nose. These irregularities rescue his features from uncanny perfection, and yet are small enough to escape the notice of most amateur artists. The eyes, lashes, and lips are so striking and demanding of attention that a lot of drawers concentrate on them and pay less attention to the shadows and proportions and distances. JA's difficult to caricature, unless one focuses on the eyes and lips, and it's a less-satisfying sketch than of JP, who's easier to caricature because of the hair, the bone structure, the eye-tilt, and the nose. He's just as difficult to render realistically, though.

Uncanny Valley gets thrown around a lot. I don't think it applies in the case of any human I've seen without plastic surgery. He's just really pretty. But 100% human. Uncanny Valley isn't perfect. It's soulless and flat.

DA era JA was especially quirky and animated, so I really don't see it.

I think it was part of the whole X5 thing. Better, stronger, faster, prettier.

He was the prettiest of the X5s, but only Alba looked flat to me. And that was because she can't act.

Mmmm. I love me some X5 Alec. He was delicious.

There's five seasons worth of JA being delicious here: [link]

And here are a couple of seasons of Misha delisha, as a bonus: [link]

Season 1 Sam should be extremely easy to render in anime style. Take your standard generic wide-shouldered guy from Macross or any similar style series, and superimpose Cousin It over his head with a wedge subtracted to show part of his face.

Screw you all.

I've gone and attempted to draw teh Ackles. This is the first time I've drawn in . . . shit, has it been twelve years? Am figuring out how to upload from my phone camera to the internet.

Further proof that fandom inspires creativity!

It's still not online yet, but I a better able to critique the anime/art (I still can't explain why I still think his eyes are close set, except maybe he has a narrow skull, and it's the proportions of that that make the proportions of his eyes seem off.)

[link] Here his chin is too narrow, his mouth too wide, the flare of his nose too narrow. He doesn't have a pointy jaw. His face is very slim, not heart-shaped or triangular. His ears are fairly flat against his head. He has high cheek bones but they aren't flashy.

Whereas Sam has become Cro Magnon Man, which is fairly easy to create a caricature of.