Dean Winchester sketchdump (Supernatural)

I normally draw fanart only for books. I typically pretentiously claim that this is because I feel that there is more scope for creativity in trying to represent a character who exists only in words. Also, since I am not a very visual person, it helps me to give the character a form in my mind. But in truth, there's another element to it as well: when I draw fanart of visual characters, there is an actual "gold standard truth" to compare my drawing against, and I end up having to face my inability to capture what I wanted to draw.

I have a fun idea which involves drawing a set of urban fantasy characters, and Dean Winchester fits too perfectly to leave him out. When I started drawing him, I totally underestimated the difficulty I'd have capturing a real character, so I ended up with a huge number of failed attempts. It's kind of depressing because I like these as "general drawings", just not drawings of Dean, but they are close enough that it's clear that they are indeed failed attempts to draw him--especially given the hair and popped collar. The only one that gets close is the "oops I started the apocalypse" expression on the bottom right. Oh well...
Suggestions on what I'm doing wrong would be welcome

And until then, I'm steadily accumulating SPN sketchdumps here.

**The rights to all of the characters in this sketchdump are owned by Eric Kripke and the CW.**