Damon Salvatore is one of those characters that most people love to hate, or that they just plain hate. And in all fairness, he has done quite a lot in his exceptionally long lifetime to earn everyone's ire. He is the very first villain that The Vampire Diaries ever had, and although he had his moments of charm and appeal, he usually buffered all of those moments with monstrously, unforgivably awful behavior.
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But if there is anything that can be said about Damon Salvatore as a character, it's that he very rarely cried over spilled milk. Even when he commits the worst of his atrocities, he doesn't tend to internalize it or feel a lot of shame about being the bad boy. There are many instances of his shamelessness, but these are the 10 most egregious examples.
Damon Salvatore has never made any bones about being a bad person, but one of his most consistently shameless moves is doing whatever he thinks needs to be done that other people aren't willing to do.
Damon really doesn't treat anyone in his life particularly well, but the people that he cares about are aware of their stature in Damon's life almost entirely because even if he does horrible things to them, he will do even more horrible things in service to them. Damon tends to be a pretty scorched earth type of guy, and he's not ashamed to do whatever it takes to win.
Part of Enzo's whole credo of survival in the Augustine prison was having some sort of revenge to live for, and after years of thought and planning Damon came up with his plot to nearly extinguish the entire Whitmore family over and over again. And although he wasn't very good at keeping his promises to Enzo, he followed through on his plan.
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And of course Damon wasn't particularly ashamed of doing this because it was all a part of the plan, and because he truly believed that the Whitmores were deserving of the punishment, but he repeatedly decimated them for the crimes of their ancestors.
The clear dichotomy between the Salvatore brothers in The Vampire Diaries was that Stefan was the good brother, and Damon was the bad one. Those reputations were somewhat earned, but Damon really did his part to be awful to people when he didn't need to be, all in the name of being the "bad guy".
Damon really was pretty bad, but a lot of the terrible things that he did were driven solely by his need to prove to himself and others that he was a completely irredeemable jerk. And obviously a lot of blood was shed in service of that.
Damon and Stefan loved each other, but Damon clearly held on to a metric ton of resentment for Stefan for a lot of different reasons. It may have been because Stefan took Katherine away from Damon in his own mind, it could have been because Stefan is the one who convinced Damon to become a vampire, or it could have been because Damon felt abandoned by Stefan when he was stuck with the Augustines.
But regardless of his motivation, Damon's need to get revenge against his brother and make him suffer endlessly was one of his main goals in life.
As soon as Damon reappeared in Mystic Falls he hit the ground running on becoming the resident town baddie. And his first major act of random, senseless, and shameless cruelty was turning Vicki Donovan into a vampire.
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Damon really just killed Vicki for fun, and because it would put an enormous strain on Stefan, Elena, and their entire relationship, and clearly Damon paid no mind to the fact that his collateral damage was an actual human being. As expected, the wild party girl had trouble adjusting to vampire life and was promptly killed by Stefan.
When it comes to protecting the few people he does care about, in Damon's mind the ends always justify the means. And if he needs to be the one to do the dirty work, he is more than ready and willing to do it.
But one of his worst moves has got to be killing Bonnie's mom. He turned Abby into a vampire simply to end the Bennett bloodline, and he didn't seem to feel particularly guilty or burdened by the fact that he turned a servant of nature into something that is an abomination in the eyes of nature.
Even Damon would probably agree, turning off his humanity and leaving Enzo to burn alive with the Augustines is probably the worst thing that he ever did in his life. He's done awful things to a lot of people, but he's never done anything worse to someone that he truly loved.
But when Damon found out that Enzo was still alive, he did not react in the way that most people would when they discovered that their best friend wasn't dead. He was incredibly unapologetic about what had happened, and he really only focused on the pain he experienced when turning off his humanity.
In the current cultural climate, being a manipulative stalker is kind of frowned upon in film and television. But when it came to Damon's obsession with Elena, his creepy behavior was downright romanticized. Frankly, Damon was Joe Goldberg from You before Joe Goldberg existed, and he transferred his centuries-long obsession with Katherine straight on to Elena once Katherine spurned him.
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Elena may have fallen in love with Damon eventually, but he never really gave her the opportunity to love him for him, and he had zero qualms about compelling, manipulating, oreven threatening Elena into whatever behavior or response he wanted.
Damon Salvatore is not someone who handles life very well. And one of his grossest, worst coping mechanisms is basically compelling women to be his girlfriend whenever that tickles his fancy.
Damon's "relationship" with Andie Star was disturbing from start to finish, but what made everything even more gruesome was that Andie herself said that she liked Damon and he really didn't have to compel her to stick around. So simply because it was convenient and he needed comfort, he continually forced Andie to be his bed buddy and blood bag for no other reason than that it was easy.
Damon's history with women has been an absolute train wreck, he's basically the living embodiment of a nightmare dressed like a daydream. And it comes as no surprise that he immediately compelled one of Elena's friends to be his girlfriend and do his bidding as soon as he got to town.
But what makes his treatment of Caroline exceptionally awful is the way that he treated her afterwards. He was still anything ranging from unnecessarily rude to incredibly cruel to someone who was a part of his squad and eventually became his sister in law, which really went to show how unashamed he was of repeatedly abusing her as a human.
NEXT:The Vampire Diaries: 5 Things That Were Changed From The Book Series (& 5 Things That Stayed The Same)
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The Vampire Diaries: 10 Most Shameless Things Damon Ever Did - Screen Rant
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