New York Cartoons

New York Cartoons

My first (and probably only) New Yorker Festival, and the tentacle that may have cost me a return invitation…

An Octopus Walks Into a Morgue…

Jason Chatfield's avatar
Jason Chatfield
Oct 24, 2026
∙ Paid

Good morning again, friend!

The New Yorker Festival is on this weekend, and for the first time in two years, they’re bringing back live cartoon improv. They skipped it last year. This is despite the fact that in 2024 they ran it on two separate nights at the SVA Theatre, and both nights sold out.

I was in one of them. I’ll tell you how it went. I’ll also tell you why I haven’t been asked back. (Short version: an octopus.)

Hey, before I kick on- A reminder: if you like my work and want to support, please consider taking out a paid subscription. It’s only a buck a week, and it makes all the difference. Really!

Fellow New Yorker cartoonist Drew Dernavich reached out in the lead-up to the 2024 festival and asked if I was available ‘for a thing’. I said yes. Of course I said yes.

I was very chuffed to be asked. Apart from being our longest-serving cartoonist player on the New Yorker Softball team, Drew’s had more than 300 cartoons in the magazine. When a man like that asks if you’re free, you are free. You cancel things. You cancel medical shit. Capiche?

The format was two teams of two cartoonists, a host and two judges. The first night (Saturday) was Drew and Carolita Johnson up against Colin Tom and Sofia Warren, and by all accounts it was a full house and a great show. We did a dry run at the New Yorker offices with the cartoon editor a week before… it’s hard to rehearse improvised cartooning, so it was possibly pointless, but we did get the gist.

As it happens, there were two separate nights, since the first sold out in record time. I was to appear the second night: Sunday, the 27th of October.

(Photo by Eugene Gologursky/Getty Images for The New Yorker)

My teammate was Emily Bernstein, a cartoonist, writer and animator who has been drawing for The New Yorker since 2019, and is a founding member of SPUMONI COOPERATIVE, a worker-owned creative agency in Brooklyn. She also has a Substack called TBH [Emily Bernstein's Substack] . Emily is very funny, very quick, and was about to be stuck with me.

Our opponents were Amy Hwang and Victor Varnado.

Amy’s been publishing cartoons in The New Yorker since 2010 and won the National Cartoonists Society’s Silver Reuben for gag cartoons in 2019. She used to be an architect. I remember her saying that when she first tried to get into the magazine, she met the then cartoon editor, Bob Mankoff. She thought she had a memorable meeting. Years later, when she finally sold her first cartoon, she met him again. He didn’t remember her. (Nothing makes you a New Yorker cartoonist faster than being forgotten by a New Yorker Cartoon Editor.)

Victor is a writer, director, comedian and cartoonist who has drawn for The New Yorker and MAD. He created Comedy Central’s The Awkward Comedy Show, which helped introduce the world to Eric Andre and Hannibal Buress, co-wrote a screenplay with Stan Lee, and has done stand-up on Conan. He is also, and I say this with love, definitely in my top five favourite Black albino cartoonists at The New Yorker. You might remember me writing about doing a gig with Victor and other cartoonist/comedians down in Pennsylvania a li’l while back.


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These are two devastatingly funny people. Emily and I were in trouble. The prize was a giant sash that said “WINNER!” - and boy, did I want that sash.

Hosting was the great Emily Flake, who has been cartooning for The New Yorker since 2008, and who I’ve written about before (Someone You Might Like: Emily Flake). She is also, as of this year, a Thurber winner, so don’t heckle her.

The judges were Chloe Radcliffe and Roy Wood Jr.

Long-time readers will remember Roy was the first guest on the live version of our podcast, Is There Something In This?, back in 2018. He started out, most famously, as a correspondent on The Daily Show, and is now an extraordinary touring stand-up with four specials to his name. He also hosts CNN’s Have I Got News for You.

Chloe is one of the sharpest stand-ups in New York, and her debut hour, Eyes Down Here, comes out this Tuesday, the 27th, on Comedy Central’s Stand-Up YouTube channel. Go and watch it. She’s brilliant, and she was very kind to me, which is more than I deserved by the end of the night.

I was very nervous.

I’d never done the New Yorker Festival before. I thought it would be a good idea to bring a date. The jury is still out on that one. On paper, it’s romantic. In practice, you’re inviting someone to watch you potentially die in front of a full theatre, and then asking if they’d like to get a drink.

We showed up at the SVA Theatre on West 23rd Street. It was full. Every seat.

And then we began…

(Photos by Eugene Gologursky/Getty Images for The New Yorker)

It was a really fun crowd.

Emily Flake took us through a lot of silly games and warm-ups, and I kept overcompensating. “Overachieving,” she called it. Every time she gave us a prompt, I went harder than I needed to, churning out more cartoons than I was asked, and by about the third game, Flake and Radcliffe and I had a whole running campaign going about it. Roy stayed quiet about my japery, because Roy knows I’ll only feed off his eyebrow-raising tongue-clickery.

I think in the end I got more boo’s than cheers for being a total dork. I also said the word ‘fuck’ in one of my cartoons, which is probably frowned upon.

Thanks for the writing prompt, Jenny-from-the-crowd.

Amy and Victor were relentless. Every time they posted one of their cartoons for the audience to judge, they’d sling a zinger at us. Throw some shade. Twist the knife a little. It was wonderful ..and horrible.

There were three columns of words. You had to pick one thing from each column and combine them into a cartoon.

There were options. Tasteful options. Clever, literate, New Yorker options. I, of course, went straight for the lowest common denominator, as I am wont to do.

I have to say, I tried my very hardest not to draw anything phallic.

This is a bigger challenge than you’d think. When you’re drawing live, in front of an audience, against the clock, the penis is always there. Waiting. Like a fire exit. Especially when you’re like me, and you’ve spent years doing a monthly live-drawing comedy show called Picture This! at Union Hall in Brooklyn.

(Which, by the way, is on TONIGHT, Saturday the 24th, as part of Animation Block Party. Come!)

It’s also difficult because I panic. And when I panic, I know what gets a laugh. I held out for most of the night. I really did.

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