The Life of a Caricature Artist Featuring Kenny Durkin!

Drawing ain’t easy. Drawing something recognizable takes effort. Drawing people is overwhelming. Exploiting peoples’ unique features in a fun and exaggerated way for their entertainment is downright insane. That’s where Kenny Durkin comes in.

Kenny Durkin by Kenny Durkin

I’ve sung Kenny’s praises before and he’s no stranger to this blog or me pestering him for all sorts of things. He graciously agreed to me bombarding him with questions again, but before that, let’s take a quick refresher course. Kenny is a cartoonist who studied Illustration at Milwaukee Institute of Art and Design. He’s performed live caricature entertainment at events across the United States for over 20 years, and drawn caricatures at Walt Disney World retail locations and special events for 15 years. He has his cartoons on apparel for AMC's Duck Dynasty, Disney's The Muppets,  and The Jim Henson Company, writes and illustrates his own online comic strip Father of the Brood, and is a proud member of the prestigious National Cartoonists Society and an award-winning Gold member of  the International Society of Caricature Artists. On a more personal note; Kenny was one of the key heads of the design team for ToughPigs Great Muppet Mural, and has been a patient and wonderful friend who has helped me out personally with tons and tons of other projects. I cannot hype this man up enough because his artistic talent is only matched by his kindness and sense of humor.

Kenny and I hanging at Gene Barretta’s home, May 2015

So let’s start with the basics: how did you get into drawing? And how did you get so good?!

Kenny: I've been drawing for as long as I can remember. The first drawing I can recall was of Kermit and Grover. I was born in 1971 and back then, there was no way of recording a television show to watch later. When the Sesame Street episode of the day was over, I still wanted to spend more time with my "friends", so I drew them. I found that was a great way to express myself creatively, and why Kermit still pops up in my drawings to this day.

Kermit the Frog as Indiana Jones and gorgeous caricatures of Frank Oz and Jim Henson

All that said, I still don't think I'm "good" at it. I think it's like having an athletic ability or being a musician. You're born with an inclination, but you still have to work at it. You have to put in the time and practice every day. And you have to be willing to fail a lot. I'm obsessed with learning to draw better, so I watch instructional videos, take courses, look at art instruction books, and I'm friends with a lot of other artists so I can push myself to soak up as much info as I can. And I've trained myself to when I'm not drawing, I'm OBSERVING. I'm looking at trees, buildings, people, animals, vehicles, clouds, everything I see and deconstructing them. I'm breaking them down into simple shapes and filing them away in the visual encyclopedia in my brain. Then I can pull them out to work out later on paper. In a way, it's a thing that I can't shut off and won't leave me alone!

We all know Jim Henson is a major creative inspiration to you, but who else inspires your artistic talent?

There are a whole lot of people who inspire me. It would be impossible to list them all. I think starting out, it was newspaper cartoonists like Charles Schultz, Walt Kelly, Hank Ketcham, Dik Browne, Jim Davis, Mort Walker, Lynn Johnston, and so many others. Later it was Gary Larson, Berke Breathed, Bill Watterson, John Hambrock, and WAYNO.

MAD Magazine was huge for me. I gobbled up everything I could from artists like Jack Davis, Sam Viviano, Paul Coker, Mort Drucker, Sergio Aragones, Don Martin, Al Jaffee, and Tom Richmond. I wasn’t much of a comic book guy, but I sought out more cartoony titles like Uncle Scrooge, Groo the Wanderer, and Zooniverse. For animation, it was of course Walt Disney, Warner Brothers, Chuck Jones, Fleischer Studios, Hanna Barbara, Don Bluth, Richard Williams, etc.

But beyond cartoons, I suppose there’s not much that DOESN’T inspire me. Anyone involved with the process of creation interests me. Musicians, singers, actors, directors, costume designers, prop builders, effects artists, folk artists and so many others. I’m all over the place.

The casts of Seinfeld and Stranger Things

When and how did you realize your knack for caricatures?

There was a magazine for kids called Dynamite that had celebrity caricatures by Sam Viviano. That was my gateway to the art of caricature. I followed him over to MAD Magazine which was a caricature–heavy publication. I studied what those artists were doing. I would ask myself, “The caricature looks like the person. Now WHY is that so? What is the artist doing that makes the likeness so strong?”. So I’d try drawing actors I’d see on T.V., friends and family, and teachers in school. My parents would get notes from my teachers saying what a great student I was because I was always taking notes. Little did they know, I was actually drawing them!

Caricatures of Muppet performers Jerry Nelson, Dave Goelz, Richard Hunt, Frank Oz, Jim Henson, and Louise Gold

What kind of lessons or classes did you have to take to go pro?

I was fortunate enough to have art classes all through grade school. In high school I took every class that was even remotely connected to art, like printmaking and drafting. I did a lot of scenery and prop building for school plays and musicals. I took classes when offered at museums like mask making.

I went to Milwaukee Institute of Art and Design and studied Illustration and Graphic Design. I also took classes there on Photography, Sculpture, Figure Drawing, Color Theory and Early German Film for some reason.

I’m still constantly educating myself. I watch videos, take online courses, read art instruction books, go to seminars, and take workshops. If you want to EARN, you’ve got to LEARN!

How quickly does it take to draw a single caricature?

It depends. When I’m drawing at events, the task is to draw as many guests as possible. I can draw a shoulders–up caricature in black and white in 1–2 minutes if I have to. At most events I draw faces and bodies in black and white, which take about 5 minutes.

A retail caricature face and body in color is about 12–15 minutes. Studio caricatures, depending on what the client and I have worked out, can take days. 

Steve Buscemi and Daniel Radcliffe

Drawing people well enough to recognize them is hard. Drawing their more prominent features to the extreme and still be able to recognize them is ludicrous. Drawing people with exaggerated features so that they’re still recognizable and doing it fast is impossible. How do you do all of that?

Practice. It takes time to get your speed up. When you first start out, your instinct is to pencil everything in, ink over the top and then erase the pencil.Once you develop a system that works, you won’t need to rely as much on the pencil (or at all). Experimenting with materials, (paper, drawing implements) that can improve your speed. Recognizability is more important than speed. In the end, it has to resemble the person you’re drawing.

Have you ever drawn someone and they reacted negatively because they felt you offended them?

Thankfully not often. One time when I was only a couple of years in, a subject got so mad at how I drew him that he lurked around until I had closed up and he followed me out to my car. Luckily security took care of him.

I did a studio piece for someone one time and after repeated redraws because she claimed it didn’t look like her, I actually TRACED her photograph. When she still insisted it didn’t look like her, I told her what I had done and she went with the first drawing I did.

You have to go into drawing caricatures knowing you’re not going to please everyone all the time. Statistically, it has to happen. So I’ll still get the occasional eye roll, but for the most part, people are pleased. They know what they stood in line for.

Is being sensitive to how someone might react to your caricature something that you consider when you draw them or is that mindset too restrictive and it’s better to believe that they should be aware it’s your job to exaggerate their likeness?

It’s tricky. When someone hires you to draw at their event, you don’t want to be the one insulting their guests, or making the host or booking agency look bad. It’s just not professional. You also don’t want to fall into the trap of drawing “genericatures” or drawing the same way over and over. You have to be sensitive and have empathy. You need to know when to lay back and be “safe” and when to kick it into gear and go for it. It’s an important skill that you have to develop over time. 

Father of the Brood 2023 and 2018 when my daughter and I made a guest appearance!

Wow! And there it is! Proof that Kenny Durkin isn’t just really good at what he does, but why he’s the best there is! Make sure you visit Kenny’s website for more great art, but also follow him on Instagram, Twitter, and YouTube too!

Thanks so much again, Kenny for taking the time to share your story and talent! I am so grateful for you and our friendship. Follow me on Instagram and Twitter, and come back on Friday for a new blog post!

The Redraw Challenge: Part II

Last week I talked a lot about growing as an artist, leveling up, getting more familiar with that growth, and recognizing when you’ve just exceeded your own expectations. None of that was possible without this week’s post which was truly an insightful exercise and the whole purpose of this two part series! When I tell you both last week’s and this week’s post almost didn’t happen, it’s not for dramatic effect. I thought I really had hit my apex and I experienced a level of frustration I couldn’t even comprehend! But we’ll get to all that. First, we need to travel back in time again. Not just to last week, but to 2009.

The iconic Alan Moore & Dave Gibbon’s comic, actress Malin Akerman as Silk Spectre II, and the 2009 Zack Snyder film

Watchmen is consistently one of the highest regarded comics of all times, and in 2009, Zack Snyder finally produced a film adaptation that has been recognized as being (in some cases too) faithful to the original source material. I’m not going to waste a lot of time on discussing whether or not it’s a good film as it’s a polarizing movie amongst fans. When I heard the announcement that it was being made however, I set out to read the comic for the first time. I therefore went into the theater with a very fresh understanding of the story and I was very thrilled with the flick. The casting in my opinion was perfect, especially with Jeffrey Dean Morgan as The Comedian, but the redesigned look of Silk Spectre II’s costume starring Malin Akerman was inspired. I had Watchmen fever and over the next couple of years, it served as a great inspiration when it came to drawing.

Of course I drew the Muppets as characters from the Watchmen! Originally featured on ToughPigs, December 2009 and Silk Spectre II, vector illustration 2014

Okay, so just to drive the point home again from last week; I found Silk Spectre II—a strong female comic hero—to be a muse and was also in the process of really honing my abilities with Adobe Illustrator, so in 2010 I had a leveling up moment by “inking” my sketches in Illustrator and then coloring them in Photoshop. This eliminated all digital debris that would be a causal problem from scanning. And hence I created what was at that time, a moment I recognized as a true level up point. I am beyond shocked now just how proud of this new drawing of Laurie Jupiter I was. Ladies and gentlemen, I am embarrassed to present to you the whole basis for this and last week’s post. Behold!

Thank you, BarbbarossaFrigyes for having the courage to say what everyone else was thinking

A second attempt in 2016

Looking back, I’m really struggling to understand exactly why I thought this was so great, but I totally did. I was still a few years away from taking those aforementioned figure drawing classes and I distinctly remember thinking how pleased I was that I didn’t use a model; backwards thinking at the time to compensate for a complete lack of understanding. I don’t need to break down how exceptionally off model she actually is here and the brush I used for the hair doesn’t even attempt to conform to the style I was going for. Still, I flaunted this piece everywhere and even used it in my portfolio! I wasn’t a young kid drawing this either! This is coming after I was thirty so I had no good reason to be so proud other than the line work. I have thought a lot about this piece ever since with an evolving curiosity in regards to everything I just mentioned and I have absolutely no good answer.

I wanted to justify my pride but eventually I couldn’t deny the best way to do that would be to redraw it. I even took a quick stab at it in 2016. This was a lot better but even my adoration of the movie was starting to wear thin. Then I started this blog and the concept immediately went into my ideas folder. “I’m a competent illustrator who’s miles beyond those days. This will be easy!” I thought. God I was so wrong. I ended up redrawing it THREE times and was completely unsatisfied thinking I hadn’t grown and maybe that doe–eyed Silk Spectre really was the best I could do.

First official attempt, 2022

Notice anything different between this first attempt and the original? Yeah, me neither! Initially I was trying to literally recreate the original with more realistic arms and newer color techniques but that was it. This wasn’t an exercise to show growth, this was modern day plagiarism from my initial drawing 12 years ago!

Second official attempt

I realized I was being too literal with my reinterpretation. I just needed to relax and approach it from a figure drawing perspective. After sleeping on it, I had my wife pose and I quickly roughed out a sketch. I wanted to keep the hair big but not like a large bob as I had done previously. The second result isn’t a bad drawing but it ain’t a good one either. What was I getting so wrong?

Third attempt

This time I took a whole week off from trying and got out of my head. I went full body on the pose and went to town hard on the coloring. I finally had an illustration that I liked but with zero soul. I was devastated. I purposely wanted to prove to myself and anyone else who read this blog that I could redraw this stupid old illustration that nobody asked for but had been living rent free in my head for 12 years. I packed up everything related to this post and moved it to the sad “Abandoned Ideas” folder on my hard drive and walked away.

Often when you work on any project—especially one you take a close personal interest in and for an extended amount of time—you get tunnel vision. You can’t see your own mistakes and you lock yourself up in a windowless room of self doubt. The reality was I was trying to not just redraw an old idea, but specifically an old idea that I felt very differently about back in 2010. The Watchmen may have remained relevant with new comics and the HBO series, but Silk Spectre II—specifically as played by Malin Akerman—was a fanboy muse from a time before everything in my current life: the pandemic, political polarization, where I lived, who I worked for, what I watched, who I associated with, what interested me, how I draw, and my daughter! Of course, I’ve talked about my daughter a lot in the past, and she proved to be an even better muse than Laurie Jupiter ever was.

A Luisa doll, a doodle I left in my daughter’s lunchbox one day, and the cool kid herself

As I’ve mentioned repeatedly before, I can draw Luisa from Disney’s Encanto from memory. Why? Because that’s all my five–year–old ever asks me to do. She’s a huge fangirl and I love how excited she gets with anything Luisa related. Plus I really like Encanto and Luisa too, but when you draw a character so often, you really want to branch out and try something different every once in a while. So when my daughter got an actual Luisa figure, I could now use it for reference. One of my favorite artists is Charles Dana Gibson, and prints of his famous Gibson Girls adorn my home and work offices, and I (as seen in the previous attempts at Silk Spectre II) love drawing people in profile. And that is when it finally hit me. I wasn’t just missing the challenge of redrawing my old illustration, I was missing the whole point.

Now it may seem like I’m asking you (and myself) to make a huge leap here to quantify drawing a Disney character in place of a Zack Snyder re–imagined Dave Gibbons character from a very adult comic. The focal point of the subject though is fundamentally the same: a strong female super hero, specifically one with great design, well thought out character traits, and a wonderful arc that helps define and evolve their world view. Then take into consideration that part of my pride in the original drawing was also surrounded by honing a new technique. In the case of Silk Spectre, it was comfortably merging Adobe creative suite products to achieve a look I had only dreamed of up until that point. With my new inspiration focused on Luisa, it’s marrying the fundamentals I learned from figure drawing and fully embracing Procreate & the Apple Pencil. To cap off the epiphany, I was determined to take the fun and cartoonish design of an animated character and change the style to pay homage to the style of Charles Dana Gibson. In short, I was going to take all that I learned and loved and play with it in a new playground with the intentions of achieving something I had never tried before.

Luisa Madrigal (voiced by Jessica Darrow), some of Gibson’s famous Gibson Girls in profile, and my sketch of my newly inspired redraw challenge subject. If you are wondering, I sketched her nude to properly achieve weight displacement and to make sure her muscle structure and limbs were accurate in length and size.

As soon as I finished my sketch (which oddly enough I did in Photoshop), I knew I was finally on the right track. I was excited, I was pleased, and I was in it for the long haul. I wasn’t going to bust this out in a day or two, I was going to immerse myself in it and take all the time in the world to achieve my goal. I’ve been amazed with Procreate and the Apple Pencil’s intuitiveness, but I also wanted to limit myself with brushes so I stayed almost exclusively with it’s ink technical pen (a halftone brush on her skirt was the only exception). Each strand of hair would be drawn as opposed to using a hair brush (not a hair brush in the traditional sense but a digital brush used to simulate human hair). I shaded using the same technical pen brush as well, painstakingly keeping all my line art clean and crisp. I also wanted to avoid my own personal bad habit of spending lots of time on the subjects face and then rushing through the rest. This meant shading and properly recognizing folds in the clothing as well. I wanted to honor Gibson’s style and that meant a lot of time staying zoomed in tight and making sure it all worked up close as well as from a distance.

In the spirit of Charles Dana Gibson (and because of all the intricate line work), I originally intended to keep it black and white, but my daughter insisted it needed color. I digitally painted it with the understanding I would pull the colors way back and the final piece made me feel even more accomplished than Silk Spectre II did so long ago. My faith in myself and this entire blog entry was thus restored. The final illustration took just over 9 hours to complete (not including all the other nonsense I wasted trying to draw Ms. Jupiter).

Man, what a fun experience! I have a huge collection of my old art I’d love to tackle and redraw, but I think I’ll put it on the shelf for now. Please follow me on Instagram and Twitter and come back here every Friday for more creative thinking experiments, interviews, and stories.