By HappyTwinFlames :
4x16 once again reminded us of Damon’s biggest insecurity: that no matter what he does, he’s “the bad guy.”
Throughout his life, Damon was constantly told that Stefan’s the good guy and he’s the bad guy. He lives within this dichotomy. What’s worse, he (just like Stefan, actually) takes this idea for granted; he doesn’t even question it. Objectively, Damon is in no way worse than Stefan, but he doesn’t see it.
Worse than that, Damon sees that no matter what he does, and no matter what Stefan does, it’s him, Damon, who remains the bad brother. These moments illustrate it perfectly well.
“I don’t do good. It’s not in me.”
See, Damon doesn’t just believe he’s worse than Stefan, he believes he’s ultimately bad. He doesn’t see anything good in himself. And even though it wasn’t actually Elena he was talking to, Elena is one of the few people who didn’t believe what they saw right away and were willing to see him for who he was.
“I’m the good guy now, remember?”
Pay attention to his smirk as he says it. Damon says it in a mocking, sarcastic way, because deep down, he doesn’t believe it. What his tone says is “I’m playing the good guy now, which is hilarious, because I’m actually the bad guy.” I think it’s significant that it happens after his last kill that we know of – but Elena doesn’t. At the beginning of the episode, we got a clear picture that Damon regretted killing Jessica – and these jokes are his personal brand of self-loathing. “You may see me as a good guy, but I know for sure who I am – and I’m nowhere near good.”
“I’m better at being the bad guy, anyway.”
This one hurts the most. Because for a long time, Damon has really been a good guy. Damon’s own kind of good, but good anyway. A loyal friend. A protector. A savior. But again, it wasn’t enough. Damon says he doesn’t need appreciation, but deep down, he does – everyone does. He tried to step out of his role of the bad guy, and it didn’t work out, as he thinks. In his mind, regardless of what he’s done, everybody is still convinced he’s a bad person, unworthy of love.
“I’m not the good guy, remember? I’m the selfish one.”
Finally, this moment is when Damon got a moment of happiness to have it taken away. He let himself believe that he was worthy of Elena, and of course, the world put him back in his place – or so he sees it. And here saying “I’m not the good guy” is just a different way to express “I don’t deserve you.”
Fortunately, Elena’s having none of it.
This is why Damon deserves a happy ending, more than anyone else on the show. Verbally, we are constantly told that he’s the bad guy, while in fact he’s not. We are also told that he can’t ever be happy and doesn’t really deserve happiness. Which convinces me that Damon must be happy in the end.