Jason's Infinite Sketchbook

A collection of every sketchbook post from the Weekly Emails. Check back every week for more…


Here are some behind-the-scenes snapshots of the above illustration for Writer’s Digest. You can see the maniacal process that led to the final concept.

And of course, one of the famous Uncle Greg.
(…who has his own theme song. Which he sings. To himself.)

Hit-n-Run Caricatures

Sneaky NYC Substack Soiree Sketches

One muggy summer night last week, fellow New Yorker cartoonist Sofia Warren and I were commissioned by


to live-draw their latest in-person soiree at one of the last iconic East Village dive bars still open: The Holiday Cocktail Lounge. Ink was spilled. Drinks were guzzled. Things got sweaty.

“Chatfield & Warren: Ink Slingers At Law”


Jesse Singal (Left), Big BARPod Fan (Right)

Jesse Singal

Sari Botton

Comic-Con Sketches

I was doing free pictures of people’s kids on the inside cover for people as a special deal with their purchase. Let me know if you’re interested in getting one for yourself or a friend!

1. I played around with using the flat line style of shows like The Simpsons and Family Guy to see if I could ape Bill Morrison’s stunning balance and composition… I think it was a fool’s errand. The man is a machine. (He’s been doing commissions and signings at Terifficon this week.)

2. Next, I tortured myself further with an attempt of landing somewhere between Joe Ciardello and Barry Blitt. Another bleh result:

3. I capped it off with a digital watercolor of a goblin (or Elf?) …possibly an Orc. He’s looking at my previous two attempts at being artsy.

Original Art © Copyright 2023, Jason Chatfield

1. I drew a very unflattering cartoon of Kim from Kath & Kim as a true crime devotée, using a Rhodium Pilot Falcon fountain pen. The nib is a nice soft extra-fine nib; the closest thing you’ll get to a flex nib on a fountain pen.

2. Next, I tried out some waterproof vs. non-waterproof ink on different paper stocks. I remember Barry Blitt saying he mixed a little non-waterproof ink/dye into his waterproof ink to still drag out a tiny bit of bleed from his line (but not so much that it dilutes the entire line).

I did try using Noodlers ink in my fountain pens to get some nice waterproof lines, but it does sometimes bind up the nib when you get lazy and don’t clean it after each use.

I’ve been using Higgins ink and Dr. Marten’s dyes, but always looking for recommendations. (Let me know if any of you have some!)

3. I switched from my usual Hunt 101 Imperial flex nib (dip pen) to a finer, more rigid crow quill nib using waterproof ink.

Subway Sketches

I’ve always preferred train travel to any other form. I sold my car 15 years ago, and If I’m not riding a bike to get somewhere in NYC I take the subway. The @SubwayCreatures account on Instagram should probably tell you why it’s such rich fodder for cartoonists.

I carry a sketchbook with me everywhere I go. It’s the thing I pull out of my pocket compulsively during moments of transit, while everyone else is compulsively pulling out their phones. (Let’s be honest, I’ve got my phone out too. How else would I be taking these photos?)

People staring at their phones on the subway is the norm… to the point where seeing someone’s eyes is a really weird thing. It’s just as well they’re so entranced— it helps me get through my drawing without them noticing. Usually. (And no, I don’t give them the drawing at the end. I’m not trying to go viral on TikTok.)

Scribbling New Yorkers on Napkins

This week, I was drawing hungry New Yorkers in a bakery on the Upper West Side.

The bakery Ole & Steen has been getting me to draw cartoons of their customers on napkins and coasters to celebrate the opening of their new locations.

I finished the day with a drink downtown at Harry’s Sidebar

I didn’t know Harry’s (at Hanover Square) had a little speakeasy attached to the side, but I do now. And I am going to eat potatoes and draw at that bar as often as the 1 Train will allow.