http://umbagog.deviantart.com/

Arggggg Jack. Jack why are you SO HARD TO DRAW!? You can't believe how many Jack faces I've been drawing trying to discover who he is, what his face looks like and his mannerisms. I've got several features in mind and finding the right proportions between them so he doesn't look like some white dude or an 18 year old kid is pretty tough. Not to mention I have to sit there and think of classic literature quips. Damn subtle personalities and complicated backstories making for non-simple character design.
This is probably the first page I'm happy with. Every other time I drew him, he looked too gay (it was the scarf, but he needs the scarf, it's a callback to Omnivorous, his creator). But just making him buff wasn't enough. And too buff and he starts looking like John. Too wiry and he'll look feminine (and then he starts encroaching on Michael's appearance). And he shouldn't look like an inbetween of Michael and John because that's just silly and lazy.

So here's some Jack with a slightly less fru-fru scarf than before. And he's got a scar from his accident years ago. And stubble.