We are thrilled that Jason Seiler accepted our invitation to be a judge in this year’s Illustration West competition. He has been creating exciting illustrations for the editorial and advertising markets for many years now, whether as realistic paintings, or caricatures with a realistic edge to them. But there is a bit more to Jason’s creativity than just his artwork, which we dive into a bit in this interview.

I first met Jason a couple of years ago when I heard he was coming to Los Angeles for a visit from his home in Chicago. He was coming to attend a short film premiere he had created art for, that just happened to be only three blocks from my home. So, I walked down the street to hopefully get a chance to meet this artist whose work I had admired for some time. We ended up hanging out much of the night, and I was pleased to walk home that night knowing I had just met a genuine person hidden inside this immensely talented body.

So, please enjoy my interview with Jason. I hope you find it inspiring as you try to reach your own creative goals in life.

Chad Frye
Illustration West 59 Show Chair

I am always amazed at how adept you are at creating amazing hyper-real caricatures of people, and then can turn around and create amazing realistic portraits of subjects as well. But how did you get to this place? What kinds of things did little Jason enjoy drawing as a kid that led him to where he is today as an illustrator?

Wow, that is a loaded question – hahaha! The easiest way to answer that would be that I have been obsessed with drawing since I was about four years old. My dad is an artist and it was all I knew – what I grew up around – so for me, that was what you did. Dad was a wildlife artist, and won wildlife artist of the year when I was seven, among many other awards. So to me, my dad was Larry Seiler, a famous and amazing artist, and I remember always feeling like I needed to be an amazing artist, too.

Admittedly, I put a lot of pressure on myself, so I was a very focused little kid. I had several sketchbooks: one for sharks, one for birds and deer, one for comics and cartoons, and eventually one for portraits, and one for caricature. I have always been focused on pushing myself to be the best artist that I could be, so doing realistic portrait paintings, and also doing hyper-realistic caricature paintings is not that strange because I wouldn’t be able to do the kind of caricature work that I do if I couldn’t also paint people realistically.

I started drawing caricatures when I was about ten years old, and at the time I thought I invented it until my dad bought me the How To Draw Caricatures book by Lenn Redman. Caricature seemed to come more naturally, and I eventually saw everyone as a caricature — I became obsessed with it, and I guess you could say, fell in love with it. It is the most honest way to capture a person’s character and essence, and there is so much you can do with it creatively. In fact, if done correctly, a good caricature can look more like a person than any photo ever could.

As a child, were you alone in your interest to draw and paint, or was there someone in your life serving as a mentor encouraging you in developing your abilities? Your father perhaps?

My dad, of course, was very supportive. He was also an art teacher for many years. My mother was also always very supportive and encouraging with my art. To be honest, I didn’t have much else going for me. I was often bullied and picked on and found it hard to make friends, so art was a refuge and a security blanket. It made me feel awesome – as if I had a super power. I even felt bad for the kids who picked on me, if they only knew who they were hitting or spitting loogies on….I guess that was my way of dealing with all that crap.

On a side note, my dad never pushed art on me, and in a way I sort of blew him off not wanting anyone else telling me how to do things. It wasn’t until I was a working professional that I actually took artistic advice from him. Now we share art with each other, and every now and then get to plein air paint together.

Do you remember when you realized that maybe you might be good enough to make illustration a career? Do you remember that first job someone paid you to do?

In my early twenties I was doing art, but was mostly at that time focused on my bands. I played guitar and sang for a few different punk bands, recorded albums, and went on tour for a few years or so. I began to notice caricature illustration in magazines, and also began to take note of certain artists who were the best at it. I would cut out pages from newspapers and magazines and study them. I saw what they were doing and remember thinking that I could do that. I just needed to work on a few things, and began to teach myself how to do what they were doing as best as I could. I would look at every little bit of a C.F. Payne piece for example, and do my own version trying my best to figure out the look and technique.

As far as remembering my first job, I had been doing commissions since I was fifteen, or perhaps even younger than that, so I am not 100% on what the first one was. As far as professional illustration goes, some of my first illustrations were done for a magazine called Cornerstone – I did spot illustrations as well as full page spreads, but only sometimes caricature. At that time I was illustrating in whatever style the art director wanted, so it was all over the place: acrylic paintings, pen and ink, watercolor – I even did a two page comic strip in the back of every issue.

There was also this religious satire magazine called The Door, or The Wittenberg Door, and I did some of my first caricature covers for them as well as spot illustrations. After that I started bit by bit, getting small spot illustrations for other random publications, until one day the phone rang, and it was TIME Magazine asking me to do something for the TIME 100, which was amazing because C.F. Payne had done it the year before. I felt like I had finally arrived when that happened.

Jason, I am always amazed at how well you work digitally, to the point of making your digital art look traditional. (I LOVED those pieces you did for West Point!) However, obviously you and I came up in the business before digital was even an option. Tell us a little about how you transitioned from traditional media to the digital realm.

Thank you so much, I really appreciate that. I was hesitant at first to work digitally, but once I tried it, I realized that as long as I didn’t abuse the computer and used it as just another way of painting, I could still create art that I felt proud of that still felt like my hand was a part of it. It didn’t take long for me to get the hang of it, and I soon decided to only work digitally for my editorial illustration work.

I continue to develop both my traditional and digital painting, and feel they compliment each other. The more I work traditionally, the more my digital painting improves, and the more I paint digitally, the more I learn about color and light, soft edges, and so on which applies to my traditional work. To me it is all about how the final image looks – if I have solved all the problems that needed solving, and most importantly, that it holds up to my standard of quality. Let’s face it, that isn’t always possible in the world of insane illustration deadlines.














Do you feel that having gone digital has given you an edge in the illustration business?

I’m not sure if going digital gave me an edge, however, it did allow me to work faster, and was a lot less stressful when it came to finishing deadlines on time and with the level of quality I was aiming for. Before I switched to digital, I was mostly painting in acrylics. I was happy with the results, but besides the tight deadlines, the work would have to be scanned in, color corrected, cleaned up from dust particles, and if changes needed to be made, it would blow my top! So switching to digital painting back in 2004 was a lifesaver.

Earlier I mentioned that your caricature work is super impressive. I’m amazed at how extreme your caricatures can be, and yet not only do you totally nail someone’s likeness, but you paint them so realistically that it seems like those exaggerated faces should exist in real life. Of the celebrities you have had to caricature for magazines or books, have you ever heard if any of them have felt a little slighted by your interpretation of them?

First of all, thank you so much. I have in fact heard from celebrities or heard from others around them second hand. The biggest one I think would be Donald Trump. I painted him in 2011, burning at the stake/his own building for the cover of The Utne Reader. I was told by a friend who spent some time with Ivanka that “her father really hated that cover.” Hahaha, I took that as a great compliment!

I’m not 100% this is actually true, seems so crazy, but I also heard from a publication that I painted a Hillary Clinton for that she had called in to ask who painted the caricature, and she said she had never laughed so hard.

Ed Helms reached out to me to ask if I could send him prints of some sketches I did of him and other characters from The Office, so that was pretty cool. He loved them, but told me he wasn’t too flattered by the double chin. Haha! He still had a good attitude about it at least.

The worst reaction by far was from Steven Tyler. Adobe hired me to paint Steven for an advertisement that was to be played live during the Oscars. I was so excited about it! I, by no means intended to offend Steven. In fact, I tried to create a younger and more iconic image of him. It is caricatured and exaggerated, but ultimately looks and feels like him. Long story short, he hated it and threatened to sue Adobe, not allowing them to use his song Dream On for their advertisement. Then later when I shared it on my Instagram (with Adobe’s permission, I might add), Adobe called and told me Steven saw my post and was pissed! They asked me to take it down, and to please wait to share it until after the Oscars. Eventually I shared it, and it actually hung proudly in the 113th Salon d’Automne in Paris which was an amazing honor!

And then you can turn around and do such a soulful, straight-up portrait of someone like that amazing cover you did for TIME Magazine of Pope Francis back in 2013.

Well, it was always a dream of mine to paint a cover for TIME Magazine, then one day I finally got a call to paint Edward Snowden for their next cover. Of course, I was so excited, and got right on it. They were very happy with the final painting, and then asked if I would be interested in painting another cover for them – Pope Francis.

I couldn’t believe it, and also couldn’t turn that down. At the same time, I had already committed to teaching a workshop in Vegas with Schoolism.com, so I started to work on my drawing of Pope Francis while in Vegas. It was a crazy time because I thought I was actually doing two covers for TIME. I had no idea that the cover was for their Person of the Year issue, and that they also had no idea who that person was going to be. Apparently Snowden was up for the cover, as well as a handful of other people, so TIME hired me as well as many other artists to paint whoever was on their list.

Not only that, but I wasn’t the only one they hired to paint the Pope. From my perspective, I thought I was absolutely painting the Pope for the cover of TIME Magazine. If I had known at the time that I was essentially competing against other amazing illustrators, I would have been freaked out a bit.

I was in Vegas for a few days, and managed to finish my sketch of Pope Francis. They approved it, and when I arrived back home in Chicago, I only had a couple days to finish the painting.

After e-mailing TIME the painting, they were again very happy with it, and said that they were 90% sure it would be the cover, and that they would let me know. That set me back a bit because I thought that I WAS painting the cover, and now I wasn’t sure what was going on. Later that day they sent me a message that said, “You’re going to want to watch The Today Show in the morning.” At this point, I had assumed that I was up for the Person of the Year cover as I was now seeing it on the news and online, but was still unsure of it because they had not said anything to me about it.

The next morning I found out for sure that I had indeed painted not only my first cover for TIME Magazine, but also the Person of the Year cover! It was one of the best days of my life! For me it felt like I had won an Olympic medal, or an Oscar…….and the Snowden I painted ended up being featured as a full page within the same issue, so that was really cool, too!

I remember that you once shared a stage with Weird Al Yankovic at an AdobeMax conference here in Los Angeles, and you had created caricatures of him, and the other speakers you shared the stage with that day. Illustration has opened up some fun opportunities now and then, hasn’t it?

Oh yes, that was pretty cool, meeting Weird Al was great! Speaking in front of nearly 8,000 people, not so great! It went well, but man, that was intense! There have been some amazing things that have come from being an illustrator, and I’m always so grateful and in awe when awesome opportunities happen and doors open simply because of my art.

Because of my work, I have had the opportunity to teach for Schoolism, which has taken me all over the place. I started teaching for them in 2006, and since then have been able to travel the world doing workshops, so for a kid who grew up in northern Wisconsin, that has always been a dream come true. I love meeting new people and experiencing other cultures all while sharing a common language of art.

I would have to say however, that my Face the Truth podcast has been an amazing gift to me personally as far as opportunities and meeting other amazing artists. I started my podcast less than two yeas ago, and because of it there have been opportunities that I never knew were in the cards.

Anyone who knows me knows that I am really into stand-up comedy. It’s something I have always wanted to do, but never had because of the amount of time and work it requires. Having a full-time illustration career plus four daughters, made doing stand-up seem impossible.

I have all sorts of guests on my podcast, from painters to sculptors, illustrators, character designers, photographers, musicians, comedians, and more! Steve Byrne is a comedian I had followed for years, and had just directed his first documentary Always Amazing, about The Amazing Jonathan. I loved it and shared a post encouraging everyone to watch it, Steve saw that and wrote me. The next thing you know, he had agreed to be a guest on my podcast. During our talk, we of course were talking about stand-up comedy, and I had shared how I have always wanted to do it. I write a lot of jokes, and said that one of these days, I have to just get up the nerve and do it. Then he just flat out invited me to open up for him at the Chicago Improv.

I couldn’t turn Steve’s offer down, so I spent the next five months writing and re-writing, trying to come up with a good five minutes. I did a couple open mics for practice, and then in December of 2019, I opened for Steve Byrne in a real packed comedy club! After doing well, he invited me to come and open for him again the next two nights. It was amazing! After that, I had the bug and couldn’t stop writing, and began going to open mics two to three nights a week here in Chicago. This is one of the coolest things my illustration has lead to, a new art form that I have a real passion for – another outlet for creatively. You never know what doors will open, and when they do open, you’ll never know what lies on the other side if you don’t walk through!

So, you are not just an illustrator. You do stand-up comedy, you host a weekly podcast, and you teach through Schoolism.com. You must be the hardest working “illustrator” around! What inspired you to get into all these other areas?

What inspired me to go into these other areas? I guess it is just in my nature. As mentioned earlier, I was in bands for many years as well, and my band from nearly twenty years ago will be recording a new record soon which I will play guitar on, as well as sing.

I always make time for my family which is most important for me, but I also feel that I have a lot of passions and creativity that need exploring, maybe for my own sanity? I feel grateful for feeling and living, and enjoy the opportunity to be able to express myself whether it be with painting, playing music, teaching, or getting a whole room of people to laugh at what I think is funny. The podcast is a way to give back a bit if that makes sense? I enjoy being able to talk with artists that will inspire and encourage others. That makes me feel great, and I learn a lot from talking with them, too.

What mountain does Jason Seiler still wish to climb? Is there a gig you would still love to have someday? I mean, besides being an Illustration West judge, of course.

Oh, there is plenty I would still love to do. As an illustrator, I want to continue to push myself and grow, continue to develop my drawing and painting skills. I want to continue to work for publications such as TIME and Rolling Stone for example, but would also love to get into painting movie posters, and that sort of thing. I also have dreams for my traditional paintings – oil paintings. I want to do oil paintings of pop culture icons as well as regular people…..to create fine art, but defined by me, not defined by the fine art world – how I see people.

I also plan to continue to do stand-up comedy once this COVID thing passes and I can get out there again to do it. I want to be good at it. I want to develop my own voice and point of view with it. It’s a challenging process that I really enjoy. It’s hard, very challenging, sometimes scary, but something that I welcome.

Over all, I want to be the best father that I can be to my four daughters. If I could leave them with anything, it would be that if you work hard enough, you can achieve just about anything.

All artwork ©2020 Jason Seiler, not for re-use without permission of the artist


Illustration West 59 just EXTENDED our Call for Entries to November 14, 2020. Submit today so that Jason can see your work! Details can be found at IllustrationWest.org!