Humor is a weird, fragile thing. You’ve probably been there—standing in a kitchen or sitting at a bar when someone drops a joke so objectively terrible that the room goes silent for a beat before erupting into genuine, painful laughter. It’s not a pity laugh. It’s the "anti-joke" effect. We are talking about unfunny jokes that are funny precisely because they fail to meet our basic expectations of what a joke should be.
It's meta.
Why do we do this to ourselves? According to the Benign Violation Theory, developed by Peter McGraw and Caleb Warren at the University of Colorado Boulder, humor happens when something is "wrong" (a violation) but also "okay" (benign). When a joke is unfunny, it violates the "rules" of comedy. If the delivery is just right—or just wrong enough—the sheer audacity of the failure becomes the benign part. You aren't laughing at the pun. You're laughing at the person who thought saying it was a good idea.
The science of the groan
Think about the classic "Dad joke." It is the titan of the unfunny jokes that are funny category. These jokes usually rely on a pun so transparent that a toddler could see it coming from a mile away.
What's brown and sticky? A stick.
That's it. That is the whole thing. It’s a linguistic prank. It lures you in with the promise of a clever riddle and then hits you with a literal observation. Your brain prepares for a dopamine hit from a clever twist, gets denied, and the resulting "short circuit" manifests as a groan-laugh.
Sociologists often point out that this type of humor is a power move. When a father tells a bad joke to his kids, he's reinforcing a social bond through shared eye-rolling. He knows it’s bad. They know it’s bad. The humor is found in the shared acknowledgment of the awkwardness. It’s low-stakes social glue.
Norm Macdonald and the art of the long walk
No one mastered the unfunny jokes that are funny phenomenon quite like the late Norm Macdonald. If you haven't seen his "Moth Joke" from the Late Show with Conan O'Brien, you are missing a masterclass in anti-comedy.
Macdonald took a simple, bleak premise and stretched it out for nearly five minutes with overly descriptive, Russian-literature-style misery. He talked about the moth's failing marriage, his existential dread, and his job at the "tax office." By the time he reached the punchline—which was a standard, decades-old street joke—the audience wasn't laughing at the ending. They were laughing at the fact that he’d forced them to endure five minutes of nonsense for a mediocre payoff.
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He weaponized boredom.
This is a specific sub-genre called the "shaggy dog story." The goal is to be as long-winded as possible, only to end with a punchline that is intentionally underwhelming. It subverts the "economy of words" rule that most stand-up comedians live by. Usually, you want the shortest path to the laugh. In anti-humor, the longest path is the funniest because it tests the audience’s patience.
Why "Bad" is the new "Good" in digital spaces
Internet culture has accelerated our obsession with the "so bad it's good" aesthetic. Look at the rise of "surreal memes" or the popularity of accounts like Thoughts of Dog. We’ve moved past the era of the polished sitcom zinger.
Now, we want irony.
We live in a world of high-definition, highly produced content. In that landscape, something intentionally low-effort or "unfunny" feels authentic. It feels human. When a brand tries to tell a "funny" joke on Twitter, we usually cringe. But when a brand posts something bafflingly stupid, it goes viral.
Take the "Juan" horse meme or the "E" meme from a few years back. There is no joke. There is no setup. It is just an image of a horse on a balcony or a distorted face. They are unfunny jokes that are funny because they mock the very idea of "content." They are the digital version of a comedian staring at the audience in silence until someone starts giggling nervously.
The physiological reaction to awkwardness
Ever laughed at a funeral? Or during a really tense meeting?
Psychologists call this a "nervous discharge." Laughter is a way for the body to regulate stress. When someone tells a joke that is deeply unfunny, it creates a micro-moment of social tension. Are they serious? Do I have to laugh? Is this person okay? When the realization hits that the joke was meant to be bad, that tension breaks. The laugh is a release of that built-up social anxiety.
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Breaking down the categories
To really understand why these work, you have to look at the different ways a joke can "fail" upward. It’s not just one type of bad.
1. The Literal Anti-Joke
These are the most basic. They strip away the metaphorical layer of a joke.
A man walks into a bar. His alcoholism is tearing his family apart. It’s dark, it’s blunt, and it refuses to play the game.
2. The Hyper-Specific Observation
This is where the joke is so detailed that it ceases to be relatable. Instead of a general observation about airline food, the comedian talks for ten minutes about the specific chemical composition of the tray table hinge. The humor comes from the absurdity of the effort.
3. The "Anti-Punchline"
This is the "stick" joke mentioned earlier. It provides a logical answer to a setup that usually requires a creative one.
4. The Delivery Failure
Sometimes the joke is fine, but the person telling it is so bad at it—stumbling over words, forgetting the middle, laughing at their own bits—that the performance itself becomes the comedy. Think of a character like Neil Hamburger. He plays a hack comedian who is failing on stage. The "unfunny" nature of his act is the entire point.
Is there a limit?
Yes.
Context is everything. An unfunny joke that is funny requires an audience that is "in on it." If you tell an anti-joke to someone who doesn't understand the concept of irony, you just look like someone who isn't funny. You need a shared understanding of the tropes being subverted.
This is why "Dad jokes" work best with family or close friends. There is a baseline of affection that allows the "badness" to be perceived as a quirk rather than a character flaw. In a professional setting, a joke that falls flat usually just stays flat. There is no meta-layer of irony to save you if your boss thinks you’re just bad at communicating.
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Using "unfunny" humor in your own life
If you want to experiment with this, start small.
Don't try to pull a Norm Macdonald and tell a ten-minute story about a moth. Start with the "literal" response. If someone asks you a "Why did the..." question, give them the most boring, scientifically accurate answer possible.
The key is the "Commitment to the Bit." If you crack a smile or acknowledge that the joke is bad too early, you kill the tension. You have to say the unfunny thing with the absolute confidence of someone who believes they are delivering the greatest comedic material in history.
The longer you can hold the "straight face," the bigger the eventual laugh will be. It is a game of chicken. You are daring the other person to call you out on being unfunny.
Practical steps for mastering the anti-joke
If you're looking to incorporate this weirdly effective humor into your repertoire, here is how you do it without just being the "boring person" in the room:
- Read the room. Only use anti-humor when the energy is already relaxed. It doesn't work well as an icebreaker with strangers.
- Vary your timing. The pause after the unfunny punchline is where the magic happens. Let it sit there. Let the silence get slightly uncomfortable.
- Lean into the literal. When in doubt, answer questions exactly as they are asked.
- Study the greats. Watch videos of Stewart Lee, Eric Andre, or Gilbert Gottfried’s later work. Notice how they use repetition and silence.
- Know your audience. If they don't value irony, don't waste your "bad" jokes on them. They'll just think you're having a stroke.
Ultimately, unfunny jokes that are funny are a celebration of human imperfection. They remind us that we don't always have to be clever or polished to connect with each other. Sometimes, being spectacularly mediocre is the most entertaining thing you can be.
Next time you hear a joke that makes you want to groan, pay attention to what happens in your chest. That little spark of frustration that turns into a chuckle? That's the sound of a joke failing so hard it circled back around to genius. Embracing the cringe is a superpower. Use it wisely.