I Might Be Wrong

I Might Be Wrong

Should Comedians "Challenge" Politicians?

After 20 years, I'm still not sure what this job is

Jeff Maurer's avatar
Jeff Maurer
May 06, 2026
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This week, Conan O’Brien and Zach Galifianakis — two of my favorites — drew some flak for how they talked about comedians’ interactions with politicians. Their conversation caught my ear partly because I’ve been on both sides of the politician/comedian interaction, first as a speechwriter, then as a TV writer. I’ve also spent 15 years thinking about how comedians should interact with politicians, but I still have more questions than answers. Here’s the clip that got me thinking/struggling again:

Some people were annoyed by this conversation, and I can see why. Here’s a representative reaction:

X avatar for @ianmSC
Ian Miller@ianmSC
Zach Galifianakis and Conan O'Brien might set a record for least self-aware conversation in human history, saying that comedians are supposed to make fun of powerful people & Trump should let himself be the butt of a joke Have they...uh, watched comedians over the last decade?
8:00 PM · May 4, 2026 · 332K Views

127 Replies · 48 Reposts · 1.98K Likes

Ian’s comment is a bit of a non-sequitur, because Trump is not letting himself be the butt of the joke. He is, in fact, trying to use state power to silence comedians — very much the opposite of rolling with the punches. Even so, I think Ian is right that suggesting that there haven’t been enough jokes about Trump is like suggesting that there haven’t been enough TV shows about hot doctors who occasionally like to have intercourse for each other.

But I’m more interested in what Zach and Conan said, especially Zach’s comment that “the job of a comedian is to challenge”. Is he right? Was he doing that in his Between Two Ferns interviews with Obama and Hillary? What do we make of the fact Conan carried the flame of the Johnny Carson ethic of political neutrality long into the partisan late night show era, but also gave a very friendly interview to Joe Biden in 2023? Is there any consistency here, and what would consistency even look like? Like I said, I’ve got more questions than answers, but maybe you’ll learn something from watching me intellectually flail.

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