How Comedians Trick People

The Fine Art of Storytelling (Comedy Mindhacks #59)

There are few things I enjoy as much as writing then telling a joke that lands. I love getting an audience to experience what psychologist Gary Klein calls “discontinuous discovery.” It occurs when an audience thinks they’re hearing one story, but the punch reveals they were actually hearing a completely different story the whole time. When that dawns on them, that unexpected cognitive leap creates a laugh.

Here’s the key: every joke I try to write will basically contain two narratives, two stories. Story 1 is, as I said above, what the audience thinks they’re hearing: the historical reality. It starts with a relatable hook, a setup that makes sense. Story 2 is what I’m actually telling them: the emotional truth, the hidden meaning, the reveal that was there all along. The magic of good joke writing and joke telling is the audience doesn’t see Story 2 until the punchline forces them to look back and realize it was always there.

Often times, when I write jokes, I start with Story 2 because I already know the emotional truth I want to land on. Then I work backwards and backfill. I try to find a relatable hook for Story 1, bending the wording and twisting the phrasing until everything lines up. I count words and syllables, test different words, and adjust the setup until both stories can coexist in the same joke.

Here’s an example from my material: “Part of my job as a pastor was doing hospital visits. It was really rewarding comforting the sick, praying with people, being there in their darkest moments. A lot of people were in really bad shape. I did what I could to ease their suffering. But the one thing I learned from all those visits is: families start to break, start to spiral, families cannot cope when… you take it upon yourself to unplug life support.”

Let me break it down. Story 1 is what the audience is hearing: I did what I could as a pastor to help. Story 2 is what I’m actually talking about: me unplugging life support. The phrase “I did what I could to ease their suffering” does the heavy lifting because it sounds noble in a pastoral context, but it’s actually describing me unplugging their life support.

Here, Story 1 has to be believable enough that the audience commits to it, while Story 2 has to be far enough away to create genuine surprise. Then they have to connect through the same words, creating what Klein describes as an unexpected transition from one understanding to another. In his book Seeing What Others Don’t,” he defines “insight” as “an unexpected shift to a better story about how things work.” I love that! These shifts aren’t about making minor adjustments or adding details. They’re discontinuous discoveries, sudden leaps from one frame of understanding to another. That’s exactly what happens when a joke lands.

The audience isn’t gradually figuring out the punchline. They’re making a sudden leap from Story 1 to Story 2, experiencing that discontinuous moment where everything clicks into place. The surprise of that transition is what creates the laugh, and maybe Klein is right that Story 2 is actually “better” since the audience finds it satisfying enough to laugh.

When I test jokes and they don’t land, the problem seems to always come down to a lack of surprise. Either people figure out Story 2 too early, or the reveal isn’t different enough from what they were already thinking. As a joke writer, I’m walking a tightrope between making Story 1 convincing enough to commit to and making Story 2 distant enough to surprise.

So, how do I know when I’ve got something that’ll work? I don’t. BUT…I do often have a hunch that guides my writing: if the joke still surprises me even though I wrote it, it’ll probably work on stage. When I can fool myself with my own misdirection, I know I’ve found the right gap to exploit.

As I said, I try to be very deliberate about this. When I write jokes or help others, I know what I’m building, which story comes first (usually Story 2), and where the gap needs to be. The hardest part is often connecting Story 1 and Story 2, finding that exploitable gap where historical reality and emotional truth can coexist just long enough before the reveal. But when I nail it, what’s so cool is that I know I made the audience take that mental leap with me. That’s super gratifying!