re: Binge watched Star Wars Clone Wars, Rebels, and episodes 2&3 for the first time

In my opinion their failure with Anakin was in the "whiny" part, not the "a-hole" part. In fact I didn't feel like they made Anakin enough of an a-hole. I've said it before and I'll say it again - Anakin should have been a character in the same mold as Dacre Montgomery's Billy from Stranger Things. He should have been a bold, cocky, arrogant son of a bitch who was stronger and more capable than everyone else and who knew he was stronger and more capable than everyone else and who could fix all the problems in the galaxy if everyone else would just get the hell out of his way with all their "rules" and "traditions" and shite. The main contrast between Anakin's character arc in the prequels and Luke's in the OT should have been that while they were both too old to begin Jedi training, Luke was humble enough to let go of everything he had learned on his own and let Yoda re-teach him things he thought he already knew, while Anakin was far too sure of himself to ever do that. Anakin's turn to the Sith should not have been because of some bad dream or any such foolishness, it should have been because Palpatine played into Anakin's weaknesses by more or less telling him, "Hey, the feelings you have are right. You are, truly, the Chosen One. You and you alone can solve all of these seemingly insurmountable problems, but only by overpowering those who can't see that you are the galaxy's only hope and forcing them to get out of your way. It's for their own good, after all." The tragedy at the end would be when Anakin finally achieved what he wanted, finally proved how much stronger he was than everyone else, he finds that instead of fixing everything and making everyone happy, he has instead destroyed the Jedi Order, killed or alienated the only friends he had ever had, helped bring down the Senate and the Republic, and killed the only person he had ever truly loved, along with the unborn children of theirs she was carrying (or so he thought). That would make the Darth Vader we see in the OT a much more sympathetic character - even despite all the harm he has done, he is still following the same empty dream of solving the galaxy's problems through strength and power, because although deep down he knows he made the wrong choice, he is far too arrogant and self-assured to admit that to himself.

Edited to clarify the last sentence.