I was commissioned during the 2015 Christmas season to do a portrait of someone’s former dance troupe leader and his partner. After sending me photos of the couple, one of the first things I said was, “Damn, those dudes are dapper!”

So, I knew right away the piece had to look stylish.

But I didn’t want it to look too slick, like some other portraits I’ve done. I wanted something loose, a little “artsy” (whatever that is), and urban without looking noir-ish.

I referenced a few of the photos (which I won’t post here, because they’re not mine) to combine different aspects of each person I wanted to include. Drawing likenesses can be really difficult, whether you’re going for realistic or a cartoon style: realistic is difficult because people will always looks for complete accuracy, and cartooning is difficult because the simplification of the subject needs to have features that are unmistakably recognizable amid the “inaccuracy” of the drawing.

I started out by sketching the position of each subject, and I knew I wanted a frame with dark buildings in the back. After I had everything placed where I wanted and the basic gestures of each figure, I focused on getting the head shapes, eyes, and noses correct, then the mouth. I remembered something artist Cully Hamner had said during an interview with artist Shawn Crystal on Crystal’s podcast, Inkpulp Audio, that they key to caricature isn’t the eyes like everyone thinks, but in the nose, mouth, and shape of the head. Even though I wasn’t doing caricature, I kept this in mind in order to get myself to pay extra special attention to those elements so that I could ensure a closer likeness.

These are the resulting pencils:

I normally use a ruler to make sure objects in perspective are accurate, then I freehand (or sometimes continue with a ruler) when I ink. However, because I needed so few grid lines, and much of it was going to be blacked out anyway, I freehanded the buildings. The buildings are taken from midtown Sacramento. I pencil on regular copy paper.

I went in for inks once I was happy with the overall structure of the pencils. I don’t normally pencil too tightly, but I pencil all the necessary elements tight enough so I know it’s “right” and I do the rest with ink. I use a lightbox, inking on watercolor paper or bristol board on top of my pencils. I do this for a couple reasons: 1) I can retain a pure copy of my pencils, 2) I can use my pencils again if I screw up the inks, and 3) I don’t have to erase anything. That last bit is a huge bonus. I inked this whole thing using a #2 Raphael 8404 brush (the good stuff!) except the bottom of the buildings, for which I used a flat Windsor Newton Sceptre Gold II, and I inked the hatched scarf stripes and the frame border a Maru dip pen (a Japanese crow quill). I used a large triangle straight edge raised by taping pennies to the bottom to ink the frame. This makes sure ink doesn’t bleed underneath the straight edge.

The photo above is the drying stage, after I put down everything I wanted, finishing with watercolors. I told my client I would do color highlights, that is, I would pick a color and fill in areas I thought could do with some color. I used blue because the guy on our right had blue highlights in his hair in one of the photos. I thought that would be a nice accent. I used watercolors because I thought they’d go good with the inking style I was using. I filled in a light layer, then before it completely dried went in to do some spot colors to give it “shadow” and depth, and I let the spot colors bleed within the first layer to make sure it had that random, spontaneous look.

There are a couple things I wish I had corrected or done differently (no, I’m not going to point out my mistakes), but overall I’m pretty happy with this.

The drawing was framed by one of the client’s friends and delivered to the guy in the scarf. I was sent a video of the opening and he was pretty touched. He liked it so much, in fact, that he commissioned me to do an illustration of his grandparents to give to his grandmother.

Here’s the final, scanned and “cleaned”: