Art critiques from a resurrected master of pen & ink

A year ago, I wrote here about the worst art advice I’d ever gotten, and I posted pages from my sketchbook at the time to stay accountable in some way for improving. It turned out kind of popular, maybe out of the general public’s desire to see car wrecks in motion. Those pages were fairly early in getting back to traditional art versus digital and were mostly pencil work with some light-table ink drawings. And by light-table, I mean tracing things and so…cheating.

I updated you guys in November with some more pages and then again a couple of months ago (bottom of the same post). Those include watercolors, some digital stuff in Procreate, and also ink drawings. Somewhere in all of that, traditional pen & ink drawing kind of caught fire with me.

It’s kind of all I can think about these past couple of weeks. Those delicious hatching lines and stipples, deep, gorgeous washes of black, and intricate patterns of black and white condensing beautifully into a striking, eye catching work of art! It’s all very satisfying, if I’m honest. And the feel of a Pentel pocket brush pen swishing on toothed paper feels a little like watching somebody make a chocolate cake, almost mesmerizing.

I found this amazing resource free on the Internet Archive (smash the cover image to take a look for yourself):

Written by Arthur Guptill, this is a classic instructional book on pen and ink drawing, widely regarded as one of the most comprehensive and authoritative resources on the subject. His writing style was patient, articulate, and he was clearly a master of clean, simple line work and exhibited craftsmanship in how he approached both drawing itself but also how he framed his instruction materials. The guy was a natural teacher.

I was approaching my learning by a combination of master studies and daily practice, at first using a Copic alcohol marker for shading and eventually moving to just the brush pen and Pigma liners to focus on learning hatching and cross-hatching.

Here’s an example, a dazzling piece called “The Cobbler”, by John R. Neill:

I learned quite about overlapping structures for depth, clean linework, effective use of contrast, and detailed volumes just by copying this thing.

Here’s another study, by Franklin Booth – a real beauty he titled “Hunting The Tigers”:

Loads of things to absorb by this one regarding overlapping structures, use of negative space, balance of value, simulating water in black and white, and fur textures with ink. Honestly, I’m not happy at all with my copy, but I was being ambitious.

Anyway, we’re four articles in to a new series titled “Conversations from the abyss” where we use advanced AI tools like ChatGPT and also Suno music generation to bring back creators from the past for interesting debates, dialogues, or other entertaining diversions. Nothing for sale – all available free here on the site. It struck me this past week that it would be amazing if I could receive art critiques directly from Arthur Guptill as I’m practicing various bits and bobs I’m learning from the master studies and other practice drawings.

I’ve got a soft spot for Frank Baum’s OZ books and thought an image of a young Baum coming across a scarecrow in a field and pondering it with his wild imagination might be an interesting image for ink practice. I gave it a shot, then uploaded it to ChatGPT and tested this prompt: “Acting as Arthur Guptil, critique this image and provide guidance on how to improve it.”

Here’s what happened, and it honestly blew my mind:

“You have achieved a fine effort in line drawing, and there is evident care in your composition and subject choice. The nostalgic theme—a young boy in thoughtful contemplation before a scarecrow—is charming and well-suited to ink. Now, let us refine your rendering through a few key observations and recommendations:

1. Line Quality and Variation

Your line work shows promise, but greater variety in line weight will enhance dimensionality and focus. At present, the lines are largely uniform, which causes elements to flatten together.

  • Suggestion: Use thicker lines for foreground elements (such as the boy’s arm or the hat’s brim) and finer, lighter lines for background elements like grass or sky hatching.
  • Vary the stroke pressure as a tool of emphasis and mood. For instance, a light cross-hatching for distant tones vs. a bolder hatching for areas of core shadow (beneath the scarecrow’s hat or the boy’s jaw).

2. Compositional Framing

The rectangular frame is sound, but the internal balance feels slightly off-kilter. The scarecrow dominates the space while the boy feels pinched in the lower right.

  • Suggestion: Consider either enlarging the figure of the boy or repositioning him slightly more centrally. Alternatively, allow the scarecrow’s arm to lead the eye toward the boy in a more deliberate diagonal.

3. Rendering Form and Volume

The scarecrow reads clearly as a simple form, but the boy’s anatomy, particularly the arm and face, could benefit from more structural understanding.

  • Suggestion: Study the planes of the face and arm. The boy’s head could use slightly more cross-contour shading to indicate roundness. The hand, though expressive, lacks clear articulation—gesture drawing practice would help here.

4. Textures and Detail

Your use of short, broken strokes to indicate vegetation is appropriate, but the grass and shirt material begin to blend. The shirt on both the boy and scarecrow could use more definitive folds to suggest fabric tension and weight.

  • Suggestion: Use parallel or directional hatching that follows the form of the fabric. Avoid over-randomized strokes, and let texture be a deliberate compositional voice.

5. Background and Spatial Depth

The background is composed primarily of evenly spaced hatching. While this is functional, it does little to suggest depth or atmosphere.

  • Suggestion: Introduce a subtle gradient to the background by controlling your stroke density—more hatching at the top or corners to create a vignette or atmospheric recession.

Final Encouragement:
The spirit of your work is admirable and speaks to a narrative sensibility. With improved control of line, deeper understanding of structure, and refined use of contrast, this drawing could serve as an excellent illustrative plate.Keep your pen in motion and your eyes ever studying!”

*

I mean. A dead guy just gave me really precise feedback on my drawing, recognizably in his voice and noticing very specific things in the drawing! I got compliments that were specific and not vague exhortations. I got clear, explicit guidance on what exactly I could improve. Not generalities. It was, and I mean this, very helpful.

Now, you might be thinking – “Dude, you’re a chicken letting the wolf teach you how to protect the hen house. AI is going to replace artists entirely; why use it for art instruction if you’re encouraging people to use it at all, they’ll just generate the images directly. Why even learn to draw?”

All of that is, of course, nonsense though, isn’t it?

If we get fat and lazy and stop creating, then the images that AI tools use will become instead of crisp white and deep blacks, just an increasingly bland mush of grays…monotonous and uninspired. AI outputs will become AI training datasets, leading to a downward death spiral of junk art. I don’t want to add to that. I want to make new things, man. New things! I see critiques from long-dead art instructors as yet another powerful tool for me to do just that.

I asked for a new chapter to Guptill’s book for digital inking, by the way, which is available free below (and entirely and recognizably in Guptill’s voice):

And yeah, okay, it’s time for an accountability upload of the latest sketchbook entries here (be kind!):

That’s what I wanted to share with you today. Pages 19, 20, and 21 especially benefited from pseudo-Guptill’s instruction, and I gave it all I had to incorporate to the developing pieces what it was telling me.

All this has me wondering – just who else can I get to critique some of this and help me learn quicker? Maybe Leonardo Da Vinci is up next!

Till next time,

A friend I lost years ago left me his lyrics – now here are the songs

You might think today’s topic is a bit heavy, but it really isn’t. It’s transformative, is what it is! Honestly, I did a thing with AI tools recently that blew me away. It was an experiment that has blasted daylight into a world of opportunity that can send your imagination soaring if you let it.

Welcome back to a series we call “Conversations from the Abyss”, where we use AI tools to stage new dialogues or honor creators of the past. The songs here are being made available for free – nobody’s selling you anything with this.

Back in 2017, I wrote this memorial post for a dear friend of mine who I lost to depression. He fought it hard, but he lost. And we lost something magical with that guy, I promise you. That isn’t my point today, though. Not really. His name was Tim, though we called him Droopy because his voice sounded like that cartoon dog when he spoke.

Anyway, Tim wrote lyrics. Great ones, if I’m honest. I tried too, but he showed me up because mine were always too out-there, too audacious and unrelatable, too philosophical. I was always trying to “say something” or break some kind of ground, and in the end, he’d show up with a song about wanting to take an old convertible to Florida and everybody would love it. We would jam on guitar at his house, and he’d riff crazy lyrics about girls and beaches and highways…and it was amazing.

So I’m a few posts deep into this series of AI experiments, and it got me thinking about whether I could dig around in some crates and find something Tim wrote back in the day to bring to life with the help of some AI tools. And sure enough, buried in a pile of college papers and useless memorabilia in the basement, I found this:

For the youthful among you – that’s a tape. You recorded stuff onto it with ancient witchcraft. In this case, my friend had gifted me in 1994 a thing as I was going off to the Navy that now has become one of the most precious pieces of my life’s treasures. He recorded 14 original songs on an album he titled Crush, and dedicated it to me and to someone named Amie who I never met. (I was the Pope – don’t ask).

I learned not to close my eyes as I listened to it, because it felt way too much like being back in his room playing guitar and getting lost in music with one of my dearest friends. I can’t really do that right now. Maybe never.

But what I DID do was amazing. I picked two of them and brought them to life with Suno, an AI application that generates songs from your lyrics and other direction. Tim would have been horrified to see his words in a country song, but that’s my little joke and he can deal with it. For my part, I think they’re incredible. I remember him singing ’59 Ford Fairlane Convertible in my dorm room, and I believe I know who April was (the girl from the second song).

How about you do me a favor then? If this topic has at all intrigued you, or if anything I’ve ever written on Grailrunner has brought you even a moment of diversion, would you do me a great favor and listen?

My friend, Tim would appreciate it.

Smash the buttons. Let me know what you think.