A good insult is a demonstration of power. A bad insult is a demonstration of powerlessness. This is true whether you’re punching up or down. (I recommend you punch up.) If you want your insults to damage your enemy and not yourself, you need to insult strategically.
Pick your audience
Is your goal making your enemy feel bad, or look bad? Those require different strategies. For the first you need to study your enemy’s values and self-image. For the latter—making your enemy look bad in front of a third-party audience—you need to study that audience’s values, and their image of your enemy.
If you want to accomplish both, try to keep your insults within the overlap. Or use different channels of attack: insult your enemy up close, and grandstand in a more public forum. The trash-talk that you mutter to the guy you’re covering in a basketball game isn’t the same trash-talk you shout at him from the sidelines. Same applies online or on the job.
Know what your enemy cares about
Learn what they don’t like about themselves, and what they’re vain about. Years ago, when I wrote for Gawker and regularly got in fights with a middle manager at AOL, he liked to say that I obviously knocked off work by 3 every day. I was working 10-hour days and took great offence to his claim, instead of delivering any number of obvious retorts. I got owned by a guy who unironically uses the word “snarky.”
Say you have a grievance with a rich greedy businessman. You might be tempted to insult his greed and wealth. But do you really think he’d feel bad if you affirmed that he loves to make money? You’d probably draw a lot more blood by finding his financial failures, and insulting him about those. Show how he’s lost by his own terms.
If you’re playing to an audience, you have more options. If they’re already on your side, they’ll probably join you in all kinds of attacks. This gets dangerous—see “don’t be a heel” below—but it allows you to attack things that your enemy actually likes about themselves, if your audience dislikes them—and make fun of your enemy for having bad values.
In 2015, internet joke man Jon Hendren showed off a bad pair of shoes: bright red Vans with leopard-print lining. His colleague David Thorpe knew the shoes were bad, and led a crowd in brutally roasting the shoes. “Shoes look like a mad doctor turned a pimp inside out.” “Man these shoes are like…what if the Black Hole Sun video was by a ska band?” “These are straight up from a porno about a clown.” Thorpe was endlessly creative, finding a thousand ways to hit the same message: the shoes are bad, Jon. Pull together a wide range of imagery about your enemy.
Vary the structure of your insults. The insults in shows like Veep and Succession are so good because they take different cadences and tones. Many start like compliments or suggestions, and sound nothing like an insult until the end. Those are like pulling your fist back before you swing it. On Succession, Tom leads Greg along with a plan: “Maybe you’ll meet a wealthy widow, and you can seduce her with your sad eyes.” In the same episode, Gerri gets Tom back when he asks her where she picked up some information: “Tom, it’s tough to have to tell you like this, but I’m in a sexual relationship with your mother. She talks in her sleep.”
Sometimes you can be uncreative on purpose, but you have to go the whole way. Repeat a phrase over and over—OK boomer—to demonstrate that your enemy isn’t worth your time and effort, and is in fact dispatched with a few words.
You can also use your one phrase as a refrain between more specific insults. Thorpe interspersed his creative insults with simple reiterations: “The shoes are a little much, Jon.” “Anyway, great shoes, enjoy.” They gave some breathing room to everyone binge-reading his roast.
But don’t land in the middle, using a few tired jokes anyone could have thought of. This makes you look like a disgruntled normo, and your enemy like someone who’s at least important enough to get “haters.”
Thorpe’s roasts almost entirely ran on comparisons to more famous signifiers. He referenced every embarrassing, retro, and heterosexually camp piece of pop culture that remotely matched those shoes.
Whatever you’re insulting about your enemy, think of more famous people with the same flaws. Those people need to be generally accepted as mockable. TV Tropes keeps a list of “acceptable targets” as gauged by public opinion. Clichéd examples include Nickelback, the Trumps, or The Big Bang Theory. But the more precise your aim, the better you pierce your enemy’s emotional armour.
Stand-up comedians do this to themselves in their openings, comparing themselves unflatteringly to celebrities. Pete Holmes loves to say he looks like an ageing Val Kilmer or a youth pastor. It works great on new audiences, because you don’t need to know Pete to see the resemblance.
Don’t get overwrought
The more creative you’re getting, the easier you can slip up. Years ago, I wrote a bad blog post, and commenters were roasting it. I retorted that they were misreading it. I didn’t want to tell them “learn to read” because it didn’t quite fit. So I came up with “Learn to parse.” That, of course, is lame as hell, something that kid from the “you frickin fricks!” video would say.
I’d just made things much worse for myself. If your insults become illegible, overwrought, or sloppy, you’ll lose. And that’s not the only way you can self-own here.
Watch your flank
Wars are lost by treating the enemy as a target only, and not an active opponent. Don’t give your enemy an opportunity for a perfect rejoinder. So: Don’t lob an insult that could be lobbed back at you. Don’t use an insult that makes you look jealous. Don’t even remind your enemy of anything they could use against you.
Do oppo research on yourself. What could your enemy use against you? What are your failures, what are your vanities? What will you say when your enemy uses these against you?
If your insults are meant for an audience, make sure yours is showing up. If you go into someone else’s replies or comments, get your friends to join you so you don’t get shouted down. Even in person, if you’re trying to embarrass someone in front of strangers, you should have friends around too.
Don’t be a heel
During and shortly after the 2016 election, there was a wave of insults based on Donald Trump’s weight. Of all the things wrong with that howling pile of hate, they chose that he’s fat. And gay. And they immediately set about making fat and gay people feel bad.
You can make fun of things your enemy can’t control, or that are also true of less bad people. If a guy is a total clown, you can call him a clown. But if your line of attack looks a lot like the attacks made by the shittiest people in the world, then drop it.
If you are straight, it’s not OK to mock someone by calling them gay, even if they are famously homophobic, because your insult still implies that you think it’s bad to be gay. The same goes for any major vector of historical oppression: race, gender, nation of origin.
It’s not OK to mock someone’s weight, because our culture is still really shitty to people it deems overweight, and the longer it’s used as an insult against bad people, the longer shitty people think it’s OK to use against good people too. This isn’t an act of fairness toward your enemy, but toward your allies.
At 5’6″, I hereby give you permission to make fun of short dudes. But you’re gonna lose some of your audience there. Short kings forever.
OK, use this wisely, punch up, and don’t spend too much of your life insulting people or you’ll eat your soul from the inside. Have fun out there kids!
It’s Evil Week at Lifehacker, which means we’re looking into less-than-seemly methods for getting shit done. We like to think we’re shedding light on these tactics as a way to help you do the opposite, but if you are, in fact, evil, you might find this week unironically helpful. That’s up to you.
This article has been updated since its original publication.