I’m known as a type designer—and fonts are pretty much what it’s all about here on my website, and in my life in general. But I haven’t always been making fonts. At various points of my career (which goes back to 1976) I’ve been a graphic designer, art director, web designer, package designer, product designer, lettering artist, and—very early on—illustrator.

Learning to Do Caricatures

My most active period as an illustrator was for Metropolis, a weekly newspaper in Minneapolis (1976-77). Patrick JB Flynn was the art director. Fairly soon after I started working for them, he asked if I could do caricatures. Caricature was something I dabbled in going back to middle school, mostly in a simple cartoon style. My inspiration came mainly from artists like Mort Drucker (Mad) and Rick Meyerowitz (National Lampoon). But I’d never done a full caricature before. Not really. But, I thought, how hard could it be?

And so I started doing caricatures for Metropolis. I wasn’t that good at first, but I got better. I was actually kind of surprised I could pull it off. Caricature is not the easiest skill—even when you can draw well. And some of my caricatures were better than others.

Above, some of my early caricature work. Clockwise f**rom the top left: economist John Kenneth Galbraith, Jr.; jazz bassist Charles Mingus; a “stoned out” Neil Young; Sylvester Stallone as Rocky with “puppy-dog eyes.”; singer Bonnie Raitt; and orchestra conductor Sir Neville Mariner.

After Metropolis, I kind of stopped doing it. I’d also dropped the idea of being an illustrator. It was easier to be an art director, think up the concepts, and let someone else do the drawing. Plus, I didn’t think my caricature style was “in.” It wasn’t the sort of thing I was seeing in the illustration annuals. I associated it with “kid’s stuff” (Mad especially) and felt almost embarrassed by it.

Getting Back Into It

Earlier this year, I made an effort to get back into drawing and other creative pursuits, and get away from staring at a computer screen all day (see my “1979” post from February). I filled up several sketchbooks over the next few months, drawing nearly every day. And then in July, I started doing daily drawings in Procreate on my 12.9” iPad Pro—quick caricature sketches of people I saw on YouTube while watching videos.

Drawing digitally—that is, drawing on a tablet or screen with a stylus—has always been problematic for me, in spite of all the money I’ve spent on Wacom tablets and Cintiqs and iPads over the years. For some reason, I just never took to it, no matter how much I wanted to. It didn’t feel as fluid and natural to me as drawing on paper. So I never did much but doodle, rarely doing a full drawing.

But I had a breakthrough while doing these quick studies. I figured out a technique for doing full caricatures that works for me, like the ones I used to do for Metropolis. In fact, it works even better.

The trick is to keep things really simple. I use the 6B Pencil brush for the line work on one layer, and the Tamar brush—sort of like painting with a sponge—for shading (and color) on a second layer. I’m careful not to change the size of the pencil brush (~60%). I try to draw at actual size as much as possible and stay loose. It all finally clicked for me.

And of course, working digitally is great for drawing caricatures compared to drawing on paper. It’s so easy to fix problems, like when proportions are off or positions of the features aren’t quite right. I’m able to work very quickly, knowing that if I make a mistake, I can immediately fix it. (Although, I might try redoing some of these using analog media now that I’ve worked out the likeness and everything digitally.)

Jimi Hendrix and Jimmy Page.

It takes me anywhere from an hour to three hours to do one of these. I’m working in both black and white and color, depending on the source photo. And, yes, these are based on specific photos, or several photos in some cases. Some of them may be recognizable—even iconic.

Neil Young and Frank Zappa.

By the end of July, I was doing a full caricature every day. This went on for almost two weeks. Since then, I’ve been doing several a week. I’ve done almost 30 of them now. Mostly rock musicians so far, but I have a long list of possible subjects in other areas, too.

Joni Mitchell and J.R.R. Tolkien.

Rediscovering Myself

I can’t believe how good it feels to reconnect with this. As an artist, knowing that you’re capable of doing something yet not doing it for years—decades even—is painful. It feels like a waste. Of course, I’m doing other things, like making fonts, which is also creatively fulfilling. In fact, I’ve often wondered if getting so busy making fonts was the reason I wasn’t drawing as much. Apparently not.

In my “1979” article, I cast a dim eye on the digital world—the world of screens and pixels—and advocated a return to doing physical things, like drawing on paper. And I have been doing that. But, ironically, getting back into drawing on paper—specifically the habit of drawing daily—led directly to finally getting some use out of my iPad Pro and Apple Pencil. In hindsight, it was all about getting back to drawing, regardless of whether it’s on a screen or not.

Anyway, all of this is a roundabout way of saying that I’m going to start sharing my caricature work online. To be clear: I’m just doing this because I enjoy doing it. It’s a side project. I’m not looking to start a new career or anything like that. Fonts are still my main gig. I just want to share something else I enjoy doing, and I hope others will enjoy seeing it.

If you’re interested, I’ll be posting the work on my secondary Instagram account (not my regular Mark Simonson Studio account, which is for official, font-related stuff). Update: I’ve also created a new website to showcase my non-type-related work: marksimonson.art.