Some people are really witty. They just manage to come up with the quickest, funniest responses in the blink of an eye, all while sprinkling it with a sense of sarcasm and irony that is very Chandler Bing-y of them.

And that’s how we end up with some of the most hilariously unhinged and weirdly diabolical insults online, the kind that will surely keep their recipients up for a few nights a year whenever they remember them. For your reading pleasure, and maybe as a way to inspire your next witty comeback, we’ve compiled a list of the most brutal online insults we could find — good luck choosing which one to add to your repertoire.

Irony and sarcasm have always been a source of what we call dark humor, but that doesn’t necessarily mean these unique insults stem from them alone. Apparently, we can trace absurdly specific insults back to none other than the father of the English language , William Shakespeare.

In many of his works, you can find examples of this kind of humor, as profanity itself often felt too weak for what he was trying to convey. Lines like “Thou art a boil, a plague sore, an embossed carbuncle in my corrupted blood” are just one of many insulting examples found throughout his extensive body of work.

But funnily enough, a back-and-forth of insults, more akin to an argument, is also reported to have existed in medieval Europe, namely through flyting, or well... Viking rap battles. Yes, you heard that right: flyting was a formal public exchange of poetic and ridiculous insults that Vikings would often throw at each other.

Many describe it as a “ritualistic game of wits” that occurred during the 5th and 6th centuries, and it even appears in Norse mythology and poems. Most insults targeted cowardice, a lack of intelligence, appearance, and even a man’s manhood and his axes. Literally and figuratively.

But to reach this level of witty humor through insults, researchers say it’s not just the work of your average Joe. Neuroscientists, linguists, and psychologists generally agree that understanding and constructing sarcasm and irony actually requires a lot of brain power and a high level of cognitive function.

Sarcasm essentially forces the brain to bridge the gap between literal meaning and actual intent, turning it into a mental gymnastics game. It requires rapid dual-path processing, meaning both sides of the brain work to process words, definitions, and context and put them together in milliseconds.