It doesn't matter whether the characters of The Vampire Diaries are Damon's friends or foes. Anytime he thinks of a witty insult to throw their way, he shamelessly lets it rip. Not even Elena is safe, and some of his best jabs are targeted towards her and his little brother.
Damon has a habit of saying things he shouldn't, but his snarkiness is one of the best running jokes in The Vampire Diaries. Because it's become ingrained in his personality, Damon drops shady burns during every episode. There are some that are particularly savage and stand out above the rest.
"Dear Diary, A Chipmunk Asked Me My Name Today. I Told Him It Was Joe. That Lie Will Haunt Me Forever."
If there's one thing that Damon loves more than anything else, it's taunting Stefan. Damon knows his little brother so well, that his burns are especially comedic due to their accuracy. When he sees Stefan writing in his diary, Damon can't help but mock him.
Stefan's entries tend to be over-dramatic and cringe-worthy, especially during the early seasons of the show. Damon attempts to match his style and pokes fun at the guilt Stefan carries with him on a daily basis. He uses a chipmunk to show his brother how theatrical he can be.
"You And Katherine Have A Lot More In Common Than Just Your Looks."
Fans might view Katherine as a villainous icon in The Vampire Diaries, but anytime a character is compared to her, it's meant to be taken as an insult. Damon does many abhorrent things to Elena, and no one can blame her for cutting him out after he kills Jeremy.
Regardless of whether Damon deserves her forgiveness, she manipulates him for information after preaching the exact opposite. Damon isn't one to talk when it comes to morality, but the burn is valid and well-deserved.
"Now I Know Why Those Hybrids Hated You. You Are Annoying."
There are an endless amount of reasons why Klaus's hybrids hate him. He turns them against their will, forces them to be his servants, and kills them if they step one foot out of line. The hybrids only follow Klaus out of fear, and whatever loyalty they have is a side effect of the sire bond.
However, after Damon spends an afternoon with Klaus, he decides that being annoying is his worst crime. Given how violent Klaus is with his hybrids, he must have been extremely irritating for Damon to come to this conclusion.
"Matt, There's A Reason We Haven't Met."
To be fair, it takes Damon seasons to even tolerate several characters, but he hates Matt from the moment they're introduced. There's not much of a reason for his initial dislike, but it continues throughout the entirety of The Vampire Diaries.
Damon sees him as a nuisance more than anything, as Matt indirectly ends up under his protection due to his association with Elena. The two can never get through a conversation without Damon insulting him in some shape or form.
"I Always Pegged You For A Lone Wolf."
Mason Lockwood is forced to become the Salvatore Brothers' enemy after Damon attempts to kill him and leaves him with no choice. In actuality, he's one of the best family in The Vampire Diaries and proves that he has a good heart even in death.
When Damon first meets Mason, he's determined to expose Tyler's uncle as a werewolf. He spends the entirety of Season 2 Episode 4, "Memory Lane," directing hilarious werewolf-related innuendoes at him. A highlight is when the group plays Pictionary and Damon draws Dances With Wolves.
"You Should Get Out, Enjoy The Sun. Oh Wait, You Can't!"
Considering that Elena has a tendency to belittle the other characters, it's hard not to find it satisfying when she's treated the same way in return. Because she continuously tries to be a martyr, Bonnie casts a spell on the Gilbert house and traps her inside.
Everyone's assigned different roles and Damon is on "Elena patrol." He finds her pouting amusing and is clearly enjoying the situation more than she likes. His mockery is light-hearted, but Damon's right to complain about the measures he has to take to keep Elena out of trouble.
"And Now The World Has One More Quarterback. Bravo, Brother."
Although many of the characters seem to think it, the world doesn't revolve around Elena Gilbert. Yet, it doesn't change the fact that Damon's double jab at his brother and Matt is one of the best lines of Season 4 Episode 1, "Growing Pains."
From a storytelling perspective, Matt adds nothing to the show. His main purpose is to end up in dangerous situations that his friends need to rescue him from. Stefan saves an unimportant character from drowning, rather than The Vampire Diaries' protagonist.
"Cheating? That Is So Unlike Him!"
There's a reason why Jeremy isn't Bonnie's best love interest in The Vampire Diaries. While their relationship is much healthier the second time around, it doesn't change why they broke up initially. Jeremy cheats on Bonnie with Anna when she comes back as a ghost, and it takes almost two seasons for him to earn Bonnie's trust back.
Damon suspects that Jeremy is repeating his past mistakes and brings his concerns to Elena, who refuses to believe it. When a teacher reveals that Jeremy has been cheating on his schoolwork, Damon is given a golden opportunity. He wouldn't be the character viewers know and love if he didn't take it.
"Talked About His Hair. I Figured It Had To Be You."
It's difficult to pinpoint where the joke originates, as it's possible that Damon has been taunting Stefan's style for over a century. Alongside dramatic diary entries and broodiness, his little brother's hair is Damon's favorite thing to make fun of.
Damon acts as though Stefan is obsessed with achieving the perfect 'do, and he comments on it at every chance he gets. Out of all the titles that Damon gives the characters, Stefan's nickname, "Hero Hair," is among the best ones.
"You Just Described Homeless People, Aging Hipsters, And Matt Donavan."
Everyone in the Mystic Falls gang gets insulted by Damon on daily basis, but Matt gets it the worst. Damon has no affection or respect for him, which doesn't appear to bother viewers. Matt is one of the heroes fans hate in The Vampire Diaries and he regresses as the show goes on.
Regardless of how he's perceived, it's difficult not to feel bad for Matt at certain points. When Damon is told to look for someone who's ragged, beaten down by the world, and desperate for a home, Matt is the first person who comes to his mind.