Drawn to NYC Stories

My first time Hosting AND Drawing the same show...

August 26th, 2026
The PIT, Chelsea

I spent last night doing two jobs badly at once, which is at least one more than I usually manage.

Henry Cruz asked me to host his show at the People’s Improv Theatre. Henry and I used to produce comedy together on the Lower East Side about eleven years ago, back when I had a wife, a full head of dark hair, and the conviction that a basement below a bar counted as a venue. The brief this time: host, do material, and draw every comedian while they were on stage, then hand them the drawing as they walked off. What could possibly go wrong?

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I have never done this before. Nobody should. It is like being asked to referee a match while sketching the players.

I’ve been sketching comics at shows and mics for a while - I do it to keep my mind occupied, if anything. (Here are a few below from this past week). But I’ve never done it to show the comics, nor while I’m hosting the show.

Here is what I learned. You cannot laugh and draw at the same time; the pen skids. A comedian’s face changes completely between a joke landing and a joke dying, and the honest portrait is the second one.

…and nobody, however seasoned, is immune to being handed a picture of themselves. They all did the same thing: looked at the drawing, looked at me, and said their nose isn’t that big. (It is.)

Eleven years ago, Henry and I were putting on shows for six people and a radiator. Last night, we were doing something different, and the audience seemed to really like it. I think I’ll do it again (against my better judgement).

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‘til next time!
Your pal,

PS. Look, if this actually did something for your brain (or at least distracted you from the creeping dread of your own inbox for six minutes), please consider restacking this and sharing it with your people. It’s the only way the word spreads.