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Creating Portraits and Caricatures with Jason Seiler

By Charles Purdy

Ever since we first worked with illustrator Jason Seiler, back in 2014 (when he created a series of caricatures for our Adobe MAX coverage and participated in a Creative Voices video profile), we’ve wanted to work with him again. Our latest “Create With” webinar provided the perfect opportunity. Here, we discuss a few of that session’s highlights, answer a few questions we didn’t have time for, and share our recording of the full session (at the bottom of this page).

Watching Jason work is a real pleasure, and we’re glad to be able to share the experience with a wider audience. Jason specializes in caricatures and portraits, as well as illustrations that fall somewhere in between those two descriptions. But no matter what you call his work, he says his goal when illustrating is to capture a person’s essence. And that’s what he does, for magazines like Time, Rolling Stone, the New Yorker, the Weekly Standard, Der Spiegel, Billboard, Guitar Player—we could go on, but you get the picture! (See Jason’s portfolio site for more.)

Mark Ruffalo illustration, on the cover of the New York Observer, by Jason Seiler
illustration of Pope Francis, on the cover of Time, by Jason Seiler
illustration of Kanye West, done by Jason Seiler for Rolling Stone magazine

Jason works both in traditional media and in pixels. For much of his editorial illustration, he works in Adobe Photoshop CC, using a Wacom Cintiq—in part because painting digitally allows him to work faster and meet tight deadlines.

But one of the things you discover when you watch Jason work is just how closely his digital techniques mirror traditional techniques: He starts with a sketch. He relies on color and line to craft caricatures, using a limited number of brushes and blending techniques, rather than using any distortion effects. And—to answer a participant question we didn’t get to during the session—he doesn’t even use masking as he works. “It’s all straight-up painting,” he says.

In this brief snippet, Jason explains his approach to sketching—in short, he likes to work fast! During our session, it took him about ten minutes to complete a sketch of director George Lucas.

“Caricature is all about capturing a person’s essence,” says Jason. In this snippet, as his George Lucas sketch comes to life, he explains his approach to drawing caricatures.

In my conversations with Jason, he stressed the importance of this painterly approach when he’s working in Photoshop. And although many of his images—even the caricatures—have a photo-realistic feel, he’s not working in a “pixel-perfect” manner. He’s judicious about where he goes for fine detail, and as he’s working, he frequently zooms out from an illustration to judge how it will look when it is reproduced in, for instance, an 8-inch-by-6-inch box on the page of a magazine.

Unlike some Photoshop artists, Jason doesn’t generally use a lot of layers; rather, he layers “paint” on a small number of layers. (But not always, as you’ll see in the Steven Tyler snippet, below.) And in many pieces, he employs an underpainting technique to help define color values and provide depth. 

So how’d Jason create rock-and-roll hair for this caricature of legendary vocalist Steven Tyler? In this three-minute snippet, he shows how he layers in color and then uses the Blur tool on hair.

Rolling Stone commissioned Jason to create a portrait of rapper Rick Ross; in this snippet, Jason shows one way that traditional painting techniques inform his digital work.

Our hour with Jason flew by (and a couple of minutes’ worth of technical difficulty about halfway through didn’t help!), and one thing I wish we'd had more time for is Jason’s Rick Ross portrait. So here’s a closer look:

progress sketches from a Jason Seiler illustration of Rick Ross

Like all of Jason’s portraits, this one began as a sketch (left). This assignment was a very fast-turnaround request from Rolling Stone. After seeing the sketch, the Rolling Stone art director asked that the sunglasses obscure the subject’s eyes—which was fine with Jason, as it saved some time. Next, Jason blocked in color (center). For this portrait, he chose a violet base. “I thought it would complement his skin tone perfectly,” he says. As he started to mix colors and values (right), Jason painted on top of his sketch lines. He keeps things pretty loose and simple at this stage, saving detail work for later.

in-progress sketches of an illustration of Rick Ross, by Jason Seiler

Once he’d finished one area of the face, Jason began painting in the rest of the face (left), layering on color as he went. Then he blocked in the hand (center). Jason is known for his subjects’ realistic-looking skin, which he creates in this painterly way. After all the colors had been blocked in, Jason began working on finer details (right). “You can see here that the nose is almost finished,” he says.

progress sketches and the final illustration of Rick Ross, by Jason Seiler, for Rolling Stone magazine

In this closeup (left), you can see the detail on the lips. “My goal with this painting was to make it feel realistic while also keeping it painterly,” Jason says. “Also, I only had one day to paint this, so I didn’t have another choice.” In the center is the finished piece; to the right, the piece as it appeared on a magazine page. To give his pieces a more traditionally painted look, Jason often employs a canvas brush (you can find many such brushes online). This painting of Rick Ross appeared in a 2012 issue of Rolling Stone, which Jason says is one of his favorite magazines to paint for. He started working on this piece at 7:00 a.m. and finished at 6:00 p.m. the same day! 

We hope we’ll be able to work with Jason again soon. In the meantime, some other questions we didn’t get to during the session addressed the professional side of things: “How do you get the attention of art directors?” and “Do you need an agent?” for example. Jason says, “An agent can help for sure, but really what I suggest—besides having a strong portfolio—is to visit art directors in person. I also suggest entering your work into shows like Society of Illustrators, for example. That’s a good way to get your work out there.”

Here’s the entire hour-long session. Enjoy—and if you find that this whets your appetite, be sure to check out Jason’s many excellent tutorials available on Gumroad, Schoolism, and Lynda.com.