Everyone has that one friend. You know the one. They walk into the room, look you up and down, and deliver a line so sharp it practically leaves a physical scar. It’s a talent. Honestly, when people search "tell me a roast," they aren't usually looking for a fight. They’re looking for a way to participate in a weirdly human ritual that spans from ancient Greece to modern-day Reddit.
Roasting is an art form. It’s also a high-wire act.
There is a massive difference between being the funniest person in the room and being the person everyone wants to leave the party. Most people think roasting is just about being mean. It isn't. It’s about intimacy. You can’t truly roast someone you don't know, because the best burns are the ones that are actually true—but framed in a way that makes everyone, including the victim, laugh their head off.
The Psychology of Why We Love a Good Burn
Why do we crave this? Why do we ask the internet, "tell me a roast"?
Psychologically, it’s about social bonding. In a 2018 study on "prosocial teasing," researchers found that within stable friend groups, lighthearted insults actually strengthen ties. It’s a way of saying, "I know you well enough to make fun of your weird obsession with vintage spoons, and I know you won’t get mad because we’re solid." It’s a safety check. It’s vulnerable.
If you try to roast a stranger, you’re just a jerk. If you roast your brother, you’re family.
We see this play out on a grand scale with things like the Comedy Central Roasts or the legendary Friars Club events. Jeff Ross, often called the "Roastmaster General," has talked extensively about how roasting is actually a form of love. You don't roast people you don't care about. You roast the people who matter. It’s a weird, twisted tribute.
When You Ask "Tell Me a Roast," What Are You Actually Looking For?
Usually, people want a "canned" roast. Something they can keep in their back pocket for a quick comeback. But here’s the thing about canned roasts: they usually suck. They feel like something you read on a popsicle stick from hell.
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"You're so ugly, when you were born the doctor slapped your mother."
Ouch. Not because it’s a good roast, but because it’s so hacky it hurts.
A real roast needs to be surgical. It needs to hit a specific personality trait. If you're looking for a roast to use on someone, look at their "excesses." Do they spend too much time at the gym but still can't open a jar of pickles? Do they have a PhD but can't figure out how to use a QR code at a restaurant? That’s where the gold is.
The Anatomy of a Perfect Roast
If you want someone to tell you a roast that actually lands, you have to follow a few basic rules of comedy.
Rule one: The Target.
The best roasts are "punching up" or "punching sideways." This is a classic comedy rule. If you’re roasting someone who is already having a terrible day or someone who has less social power than you, it feels like bullying. If you’re roasting your boss (who has a good sense of humor) or your incredibly successful best friend, it’s hilarious.
Rule two: The Truth.
A roast has to be based on a kernel of truth. If you tell a skinny guy he eats too much, it’s not a roast. It’s just a lie. If you tell a guy who is obsessed with his new Tesla that he’s basically driving a giant iPad that he can’t even fix himself, that hits home.
Rule three: The Rhythm.
Comedy is math. It’s about the setup and the "turn."
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- Setup: "I love your new house, man, it’s really great."
- The Turn: "It’s so brave of you to live in a place where the primary architectural influence is 'divorced dad's first apartment.'"
Why Reddit’s r/RoastMe Is a Masterclass in Masochism
If you really want to see the "tell me a roast" phenomenon in the wild, look at r/RoastMe. It’s one of the most popular subreddits for a reason. Thousands of people post photos of themselves holding a sign, literally begging strangers to tear them apart.
It’s fascinating. It’s a digital coliseum.
What’s interesting is that the roasts that get the most upvotes are never the ones about physical appearance alone. The winners are the ones that construct a whole life story based on a single photo. They see a guy in a beige cardigan and suddenly he’s "the human embodiment of a room temperature glass of water." That’s a roast. It’s creative. It’s specific. It’s devastating because it feels like a character assessment.
The Danger Zone: When Roasting Goes Wrong
It's easy to cross the line. Honestly, most people cross it way too often.
The moment a roast touches on something someone is genuinely insecure about—and can't change—the laughter stops. There’s a "vibe shift" in the room. You can feel it. If you roast someone's laugh, they might never laugh naturally around you again. That’s not a win. That’s just being a sociopath.
Professional roasters like Nikki Glaser or Anthony Jeselnik get away with it because the audience knows the "contract." The contract is: we are all here to be mean for sport. In real life, that contract is rarely signed. You have to read the room. If the person you're roasting isn't laughing, you didn't win the exchange. You lost the relationship.
How to Build Your Own Roasts (The Pro Method)
Stop looking for lists of roasts online. They are outdated the second they are published. Instead, try this. Think of the person you want to roast. Now, answer these three questions:
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- What is their most "extra" trait? (Are they too loud? Too cheap? Too into crypto?)
- What does that trait remind you of? (A used car salesman? A Victorian ghost? A golden retriever on espresso?)
- How can you link those two things?
Example: Your friend Dave is obsessed with his beard. He spends forty minutes grooming it.
The Roast: "Dave, I love the beard. It’s impressive. It’s like you decided to grow a personality because you couldn't find one at the store, but you ended up looking like a lumberjack who’s allergic to trees."
It’s specific to Dave. It hits his vanity. It’s funny.
The "Tell Me a Roast" Hall of Fame
Historically, some of the best roasts didn't happen on a stage. They happened in letters or over dinner.
Take Winston Churchill and Lady Astor.
Lady Astor: "Winston, if you were my husband, I would poison your tea."
Churchill: "Nancy, if I were your husband, I would drink it."
That is the pinnacle. It’s fast. It’s witty. It uses the opponent’s own logic against them. That’s what you should be aiming for. Not a "yo mamma" joke from 1994.
Actionable Steps for Your Next Verbal Sparring Match
If you're going to dive into the world of roasting, don't just wing it and hope for the best. You'll end up losing friends.
- Start with self-deprecation. If you can't roast yourself, you have no business roasting anyone else. It signals to the group that you’re "in on the joke" and that you don't take yourself too seriously.
- Observe the "Three-Second Rule." If you think of a roast, wait three seconds. If it still feels funny and not just cruel, say it. If it feels like it’s going to actually hurt their feelings, keep it in your head.
- Watch the greats. Go watch Don Rickles clips on YouTube. He was the master of roasting everyone in the room without making them hate him. Pay attention to his smile. He was always smiling. It showed he was playing a character.
- Focus on choices, not traits. Roast someone for the weird shoes they chose to wear or the fact that they still use a Hotmail account. Don't roast them for things they can't help.
- Know when to end it. A roast is a spice, not the whole meal. Give one good jab, let the laugh happen, and then move on. If you keep going, you’re just badgering someone.
Roasting is essentially a high-stakes game of "tag." You want to tap the person, make them "it," and then run away before they can get you back. If you do it right, you aren't just telling a joke; you're creating a moment of shared, hilarious honesty. Just make sure you're ready for them to roast you back. Because they will. And if you can't handle the heat, well, you know what they say about the kitchen.
Keep your roasts clever, keep them quick, and for the love of everything, keep them original. The internet can give you a template, but the best "tell me a roast" moments come from the world right in front of you.
Next Steps for Better Wit:
- Practice Active Observation: Spend one day looking for the "absurdity" in your daily routine. Why do we all stand in line for coffee like we're in a trance? Why do we use "Best," as an email sign-off when we actually mean "I am ending this interaction now"?
- Study the "Rule of Three": In comedy, you give two normal examples and then a third absurd one. "He’s smart, he’s kind, and he looks like he’s not allowed within 500 feet of a Chuck E. Cheese."
- Record and Listen: If you're serious about being a "funny" person, listen to how you tell stories. Are you dragging them out? The soul of a roast is brevity. Cut the fluff. Get to the burn.