While The Vampire Diaries begins as an overdramatic teen drama, it slowly evolves over the course of its first season. It takes a decent number of episodes for the shift to become obvious, but it occurs when Damon Salvatore transitions from a villain to an antihero who acts as the comic relief.
Damon has several characteristics that make him stand out from the rest of the cast, and his sense of humor is unparalleled. He constantly makes witty comments, and his tendency to nickname the other characters is the best running joke in The Vampire Diaries. Due to how hilariously accurate his nicknames can be, some of Damon's some of them stand out as his best.
Bonnie The Teenage Witch (Bonnie)
If it were up to Damon, Sabrina the Teenage Witch would star Bonnie Bennett. Damon uses Bonnie's heritage to crack endless jokes, and she has a particularly large number of Damon-created nicknames. While their relationship starts off hostile, they become one of the most important people in each other's lives.
When Damon chooses to save Bonnie over Elena, he claims that he's not out of nicknames for her quite yet. Although there are too many witch-related names to count, "Wicked Witch of the West" and "Witchy" are honorable mentions.
Vampire Barbie (Caroline)
Out of all of Damon's nicknames, "Vampire Barbie" is one he uses most frequently. Caroline originally comes across as shallow and materialistic, and her mean-girl attitude makes it easy to dismiss her. Everything changes after she transitions, and Caroline ends up having one of the best character arcs in The Vampire Diaries.
Damon might use "Vampire Barbie," to make fun of Caroline, but it reflects her personality surprisingly well. While vampirism helps her become stronger and more confident, Caroline still enjoys being the head cheerleader and planning school dances.
Hero Hairdo (Stefan)
Anytime the opportunity provides itself, Damon jumps at the chance to make fun of his little brother. He takes a particular interest in mocking Stefan's hair and sense of heroism, which is where the nickname "Hero Hair" originates.
While there never seems to be anything wrong with Stefan's hairstyle, Damon continues to comment on it throughout the series. It's easy to see how "hero" is an applicable title, as Stefan has a strong moral compass and always wants to do the right thing.
Barbie Klaus (Rebekah)
Damon creates Rebekah's nickname by combining her resemblance to Caroline with her relation to Klaus. Rebekah finds herself in competition with "Vampire Barbie" and their feud is partially brought on by how alike they are.
She and Caroline enjoy the same clubs and activities, and both possess the need to be in control. The shared nickname is fitting, and because she's an Original vampire, Damon considers her to be the Barbie version of her older brother.
Detective Dumbass (Matt)
Matt may be a main character, but he's also a hero fans hate in The Vampire Diaries. Damon doesn't care what most people think of him, and he has no problem being blunt around those he doesn't like.
While "Detective Dumbass" is a rude thing to call anyone, Damon hits the nail on the head. Matt continuously pokes his nose in places it doesn't belong and ends up doing more harm than good. His attempts to help his friends usually result in Matt being kidnapped and used as leverage.
Tween Wolf (Tyler Lockwood)
No one can replace Scott McCall as MTV's Teen Wolf, but Damon seems to think that Tyler fits the criteria. Although he would be a wildly different protagonist than Scott, Tyler's plot in The Vampire Diaries proves that he has plenty of stories to tell.
It's especially funny that Damon refers to Tyler as a "tween," given that Tyler is well into his teenage years. But that's because Damon sees all of the main characters as children, and since he's a 200-year-old vampire, no one can really blame him.
Lying, Mama-Killing, Dagger-Happy Brother (Klaus)
It's a little long for a nickname, but "Lying, Mama-Killing, Dagger-Happy Brother" is the quickest and easiest way to summarize Klaus Mikaelson. He has significant character development in The Originals, but Klaus is the most powerful villain in The Vampire Diaries.
Elijah might be a man of his word, but the same can't be said for his brother. Klaus lies to his family about their mother for centuries and never appears to carry any guilt. Rather than face the consequences of his actions, Klaus daggers his siblings to avoid unwanted conflict.
Pouty (Elena)
All of the characters in The Vampire Diaries have their good and bad qualities, and Elena is no exception. Damon has plenty of nicknames for the woman he loves, and while some are affectionate, he also has those that he uses to taunt her.
Elena understands loss better than anyone, yet on a more minuscule scale, Elena cops an attitude when she doesn't get what she wants. Whether she's right or wrong, "pouty" is the perfect way to describe her facial expressions. It's a look that Damon appears to know all too well.
Bon Bon (Bonnie)
Bonnie is one of the few characters whose nickname is also a term of endearment. Damon and Bonnie spend months in forced proximity, and their time in the prison world causes them to bond.
Much to viewers' surprise, the two become best friends, and many fans believe that Damon and Bonnie are soulmates in The Vampire Diaries. While Damon has plenty of insulting nicknames for her as well, "Bon Bon" is used to exemplify their closeness.
Buzzkill Bob (Stefan)
It comes as no surprise that Damon has the most nicknames for Stefan or that he calls him "Buzzkill Bob." Stefan doesn't attend social events by choice and definitely isn't the life of the party. While taunting his little brother is Damon's favorite hobby, Stefan makes his work too easy.
His brooding, over-dramatic diary entries, and unreadable facial expressions only add fuel to the fire. These are all characteristics of Stefan that viewers have come to know and love, but the show needs to make fun of itself in order to be taken seriously. By using Damon to acknowledge the more theatrical aspects, The Vampire Diaries upholds its integrity.