The Comedian's Paradox
The Strange Thing About "Truth" in Stand-Up Comedy (Comedy Mindhacks #56)
Every time I step on stage, I look at it like I’m entering into a strange contract with the audience. I need the audience to believe me, BUT…I also need them to know I’m repeatedly setting them up to be tricked. It’s really a strange thing when you think about it! It’s what author Will Kaufmann calls this “The Comedian’s Paradox.”1 And honestly, a comedian’s entire career really depends on maintaining the tension between these two contradictory positions: requesting an audience’s trust while acknowledging that you yourself, as a comedian, do not deserve it. Kaufmann describes it as “a wearying task,” and, frankly, he’s right. Let me explain but first, let me tell a joke I wrote that’ll help in that endeavor.
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 1 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.
So, with this joke, when I tell an audience about my time as a pastor doing hospital visits, that’s true. It’s totally true. When I speak of entering into the dark moments, the prayers, and being with the families in crisis, that’s completely real. But when insinuate that I unplugged someone’s life support… that’s just a joke. In essence, I’ve told you truth to earn your trust. Then I immediately exaggerate in such a way that I reveal to you that I really don’t deserve your trust because I’ve tricked you. And I’m going to keep tricking you.
As I’ve written about on this site before, this works because in comedy historical facts are not really what matter. Nope! It’s the emotional truth that matters. And the emotional truth is 100% accurate: if I actually did pull the plug, families would be irate. That’s the real insight. So, when I’m telling a joke, the setup has to be real to life, real to my persona, and emotionally honest. The punchline has to be playfully inappropriate.
That phrase, playfully inappropriate, is specific for a reason. As Jared Volle has pointed out, it’s exaggerated enough that an audience knows it’s not factually real. But it’s also not completely out of the realm of possibility. That’s the sweet spot. If I miss it in either direction, the whole thing collapses. And this really is where a lot of comedy just breaks down or doesn’t work in the first place.
I work clean. That’s who I am in real life. But it’s also a choice that fundamentally alters The Comedian’s Paradox. Here’s why: when an audience comes in knowing I won’t violate certain boundaries, their guard comes down. They’re willing to play along more. They don’t have to brace themselves for shock. A lot of shock humor earns nervous laughs. After once or twice, however, people often put their guard up. Laughs blocked! That’s because they’re laughing at the shock itself, not from genuine surprise at the emotional truth.
With clean comedy, unless I go the hokey silly route, an audience’s guard stays down and they’re ready to laugh. That’s when the paradox actually works. I can deceive listeners more effectively because they trust me more deeply. This is part of the reason I like to start with self-deprecating material. I don’t merely do that so I’m likable. I do it to establish the trust-deception contract early. I show an audience I’m willing to be the butt of the joke before I make anyone else, including them, the butt of it.
If I skip that crucial step, I will likely come off as a jerk immediately. Audience members need to see that I have a warm persona. They need to know I’m not too serious, that I’m playful. That establishes my style. Then when I hit them with something playfully inappropriate, they’re already on board.
This is helpful in another way, too: when a joke misses that sweet spot and lands in just “inappropriate” or just “playful,” I know instantly. Sometimes it’s no laugh. Sometimes it’s a groan. Sometimes it’s a laugh that feels wrong. Then I have to recover which is often possible, but not always. I’ve found that, when this happens, the best move is to just acknowledge it, to address the elephant in the room. It’s likely the best and quickest way to win them back. Otherwise, it’s like I just pulled the plug on my own life support.
INSTAGRAM: Friends, I’m trying to grow my Instagram presence. It would mean a lot to me if you could follow me HERE. Thanks.
JOKE WRITING COURSE: By the way, if you have any interest at all in learning about your persona, how to write some jokes, or doing stand-up comedy, check out my online joke writing course, “The Joke Writer’s Lab,” HERE.
Will Kaufman, The Comedian as Confidence Man: Studies in Irony Fatigue (HLLS; Detroit, MI: Wayne State University Press, 1997), 30.


