I enjoyed reading you guys discussion on Chuck. To me its pretty simple. Chuck is jelous of his brothers ability to make everyone like him despite his shady character, while he sticks to the law and tries to be what he deems a decent person yet the same doesnt happen for him. He is fueled by his jelousy and uses his knowledge of the law as a weapon to stop his brother at every turn. While Jimmy is obviously shady as shit he has redeeming qualities and at various points in his life already has tried to turn himself around and be legitimate. Chuck fails to realise that most of the shady things Jimmy does are because of his actions against him (because of his own jelousy) and completely ignores all the nice brotherly things Jimmy does for him.
You end up with this really interesting dynamic where you have one guy who breaks the law in various ways for multiple reasons but is very likable and often has good intentions (doesnt make it right but it does create sympathy and understanding). Meanwhile you have his brother who tries to be "good" and use the law to the letter but is almost entirely unlikable because he uses this knowledge to stop his brother at every turn because of jelously alone.
Glad you enjoyed it, since I always like to spark interesting discussion, even if not everyone agrees with me.
I agree with your assessment that a big part of Chuck's frustration and resentment comes from the fact that he's not well liked and he can't seem to do anything to change that. This pops up in a lot of ways, like how Rebecca enjoyed Jimmy's jokes, while when Chuck tried to make his own, he couldn't make her laugh, to something like his mother calling out for Jimmy (who was off getting food), while he was the one who was actually
there for her. Stuff like that, he's basically outright sick of being the unwanted one when he tries his hardest.
I'll probably do a write up on that one of these days, but I want to see if we get any more tidbits on Chuck and Jimmy's past this season first. But it's not only good character writing, it's deliciously meta-textual. Chuck lashes out because he isn't liked like Jimmy is, both in universe and by the audience*
*Except Howard. I do wonder if Howard is his only friend. And if he's a genuine friend or more of a close and respected colleague.