I don’t remember exactly when I first met Dale but I am fairly sure it was at the Society of Illustrators at one of the openings probably around 2006.

I lived in New York and he was in Massachusetts so I would only see him at the various Society or American Illustration openings and parties. When I moved to Massachusetts, I had the opportunity to hang out with him and the other local illustrators more often.

Dale’s work astonishes me. I know, I know, this is an interview with a friend so of  course I'll say something like that. But its genuine. I've attempted the type of work he does in my early discovery days of my career and I am just not good at it. I don't have the patience. When I look at the work, it's like magic to me.

Dale had a solo show a couple of years ago which had over 50 pieces of both digital work and huge traditionally painted pieces which reminded me how good he actually is at what he does. From straight up portraits to making a statement about a social or political issue, there’s always something to take in with each of his pieces.

One of many things I admire about Dale the artist is that he tries new things frequently pushing his abilities as far as he can. I have a lot of respect for that. Dale always seems to be moving forward. Accomplishing one thing, then on to the next. He's even started teaching at Lyme Academy of Art to push himself even further learning what it means to be an educator and sharing with the next generation, how to make being an illustrator work.

From the start, I discovered Dale is an immensely likable guy. He is honest and direct but kind in every way. He’s always got a funny quip about a situation ready for any conversation or a self-depreciating comment ready to go when he gets a compliment about his work. He is rather worldly and knowledgable about so many different thing as well which means there is always something to talk about. I think that's also just part of being an illustrator. We get the type of work that requires us to pay attention to the issues in the world.

Dale has the ability to feel like you’re part of a group and makes sure you’re involved and part of the conversation. His wife, Maria is the same way as well. Actually, she is a black belt at it. They always seem concerned about how people feel. As if they're trying to tap into something deeper in each person rather than the superficial.

Here's part of our recent conversations.

Dale Stephanos

All artwork
© Dale Stephanos
All Photography © Scott Bakal
Equipment: Canon 5D Mark II; Canon
 24-105 Lens; Two Canon Speedlite 580EX II Flashes; Umbrellas








Some time ago, we were talking about our histories of how we started out as illustrators. I think I heard you say the other day that your current illustration work is cartoons and caricatures on steroids. Starting out as a cartoonist, the first obvious question is why you started as a cartoonist? What and who were the influences that made you?

I don’t come from an artistic family, so my first exposure to any kind of visual art was in the form of cartoons simply because that was what was available. The main ones are Jack Davis, Mort Drucker, Chuck Jones, Tex Avery, Charles Schulz, Pat Oliphant, Jeff MacNelley, Thomas Nast, Daumier, Mike Ploog, Neal Adams, Ralph Steadman, Gottfried Helnwein (that Scorpions cover!) Drew Struzan, Norman Rockwell, David Levine, C.F. Payne, Mark Fredrickson, Andrew Wyeth and so many more.

I loved the Sunday comic’s pages, MAD and the National Lampoon magazines and Saturday morning cartoons. The most important to me was the Warner Bros. cartoons. Even as a little kid I sensed that there was something much bigger than my young brain knew exactly how to appreciate behind those Bugs Bunny cartoons. The elegance of the way Bugs was drawn knocks me out to this day. I also loved the editorial page cartoon in the Boston Globe by Paul Szep. I looked at those cartoons and caricatures of Szep’s and they really floored me. I thought it was cool to draw people in power, knocking them down and kicking their teeth in publicly. He was winning Pulitzer Prizes for it! That made an enormous impression on me. I learned how to draw caricatures by copying Szep's drawings.







There are so many illustrators that were inspired by those cartoons as a young kid. I certainly was. That’s a lot of visual stimulation you had as well. When was the time you started taking some of these cues from around you and applying it?

When I was in the 6th grade I was asked to draw the front page of our little Hadley School yearbook. I had to draw Mrs. Goldstein, who was probably in her late 50’s, but to a 6th grader, she might as well have been 90 years old. It was 1976 and the bicentennial was the overwhelming theme in the country, so I brainstormed up the idea of putting Mrs. Goldstein in a rocking chair and sewing the flag like Betsy Ross. I was very proud of this idea.

When Mrs. Goldstein called me into the coatroom for a word in private I smiled, anticipating her looking into my eyes and whispering “Dale, you are a genius!” and embracing me, tears of pride in her eyes. Instead she showed her teeth and said something like “Look, Buster, I am NOT an old lady and I won’t have a little brat like you drawing pictures of me in a rocking chair”. She told me to go back to the drawing board and start again. I don’t remember how many ideas I came up with, but each one was shot down until I ended up just drawing a flag. I guess that was my first bad experience with art direction.

I wasn’t disappointed though. The dustup made me realize that even though I was playing with what may have appeared to be a toy gun, it shot real bullets. I’ve always tried to keep that in mind.







When did this start becoming a real thing that created a living?

One day at Quincy Market I saw that the crowd was watching a couple of guys drawing people. They had tip cups that were overflowing! I hung around and asked them how I could get into what they were doing. They were very kind and gave me a card with a number to call. I went down to their office in Quincy and the owner of the company, Rich Hill, put a marker in my hand and said, “Okay, draw me”. There was another guy in the office. A thin, almost translucent, squinty guy with a whiny voice who rolled his eyes and announced: “Oh God. Another one! When will this parade of sadness end?”

Oh, one of those kind of guys…!

Yeah. I’m sweating and I have a death grip on the sharpie and this guy is heckling me. I finish the drawing streaked with the sweat that dropped off my nose and I hand it to Rich and put my head down. 

 “Hey, this is good! I’m pleasantly surprised!”
“Hey Bill, look, he’s better than you” Rich said to the pale squinty guy.
Pale Squinty Guy put his head in his hands and said: “No, no, make it stop” over and over.

 I later realized after getting to know him, Pale Squinty Guy was the funniest person I’d ever meet. His name was Bill White. He would go on to work on Ren and Stimpy, Richie Rich, Casper the Ghost, Sonic the Hedgehog comics as well as his own titles. Sadly, he passed away only a couple of years ago.

I stayed with that company full and part time for 13 years drawing at Quincy Market, Bar and Bat Mitzvahs, corporate events, colleges, private parties and the like. It was a great proving ground. I had to introduce myself to someone new every 5 minutes and have a conversation that would hopefully make them laugh and put them at ease. Then I needed to draw a reasonable likeness of them, and think up some kind of gag for the picture. This was always in public with a crowd over my shoulder. The deadline was every 5 minutes. It was wonderful and it was horrible.













Thirteen years is quite a while. Was there a shift that led you in a different direction?

The job was cool because of all the travel. I visited every state in the lower 48 except for Oregon and Washington. I got to the point where I really wanted something more solid where I could do work that was more thoughtful and finished.

While I was on the road, wherever I was, I enjoyed the local newspaper’s editorial cartoons and fantasized about being able to do that at home. This was around the time of the first Gulf War and I had plenty to say about it. I drew up a batch of cartoons and sent them back to my local paper, the Haverhill Gazette. To my shock, the editor called and asked to buy them, and asked if I wanted to do 3 per week.

After I felt I had developed a bit I started sending copies to the national papers and magazines hoping they would reprint them. Again, to my disbelief, I started getting cartoons reprinted in the New York Times, Los Angeles Times, Newsweek, Washington Post. USA Today even asked me to contribute on a regular basis! Then I got up the nerve to ask Jerry Holbert, the editorial cartoonist for the Boston Herald, to put a good word in for me and I was asked to be a regular contributor to the Herald as well. That lasted for 13 years.

It’s a good time-honored lesson. Believe in what you want to do and put it out there.

I feel that cartooning chose me as much as I chose it. It’s my native artistic tongue and no matter how well I learn to speak in the language of painting, I’ll always think like a cartoonist first. For me, painting is very technique oriented. Cartoons are more about the idea. I think that’s why illustration was a logical next step in my evolution. 







How did the switch happen?

Mid-way through my stint with the Herald they started asking me to do drawings for the Op-Ed page. I was doing knock offs of David Levine, Jack Davis and Mort Drucker simply because that’s all I really knew or had been exposed to. I really liked doing them. I began to take my time with the drawings, trying to make them as “good” as I could. After a couple of years I pulled together a few pieces of that kind of thing and sent them around to the bigger newspapers that had reprinted my cartoons. I did pretty well with that. By this time I had begun self-syndicating my work.

I was approached by the late Jay Kennedy at King Features who was a really great guy and a true champion of cartoons and cartoonists and asked me to be in their stable of cartoonists. When I looked at the numbers though, I realized that I could make more money on my own if I just hustled and won a few loyal client papers.







That takes guts to walk away from that sort of offer. King Features is pretty major.

It worked out pretty well though. In a few months I was selling a package of 3 cartoons and 6 caricatures per week to about 25 papers. Not huge money, but significant enough to make it worth my time. I remember really longing for a fast, efficient way to get the newspapers my work faster than printing them and mailing them out. Today we call that email. I needed speed because editorial cartoons have a very short shelf life. If a month goes by, even the artist might be fuzzy on exactly why he or she thought the cartoon was such a brilliant idea. 

Current events and politics are like that. If you’re not pushing it out there at that moment, no one will be interested when the next news cycle happens.

Right! Around this time I noticed that the Boston Phoenix was using a lot of illustration on its cover. Being well versed in local politics, I did a colored pencil caricature/cartoon of then Governor Bill Weld to accompany a story they did that week.

I called the art director at the time and asked if I could come down and show her my portfolio. At the time, my portfolio was mostly black and white ink drawings and some hacky colored pencil things. While I sat in the waiting room I looked up at the covers they had framed on the walls. One that really impressed me was by Robert Saunders. It showed a guitar player who was in the process of drawing the guitar in his lap. It was really beautiful. I stared at it and considered just leaving, thinking I had no business being there.

Before I had a chance to bolt, the art director came out and quickly looked through my portfolio, not saying anything. “Okay, we’ll give you a call if you need anything”. I thought that was the last I’d hear from her. The next day she called and asked if I’d do a cover. My jaw was on the floor. I continued to do covers for the Boston Phoenix, Providence Phoenix and Portland Phoenix until they all closed fairly recently. Kristen Goodfriend was the person I worked with most often and she was really kind, even when I did a lousy job. There came a point where my quotes were getting way too high for them. Because they gave me so much work early on, I decided I’d go with loyalty over money. Over the years I did hundreds of assignments for them, both covers and tons of interior work.


Those long-term clients are gold.

It’s interesting that you did some colored pencil work for the covers. When did it start becoming more refined in the way you’re working now?

I slowly began to accumulate better work and started working in acrylics with an airbrush which was a big leap because for the first time, I wasn’t using just line. It was all value and color, which was scary and exciting to me. I sent out some samples and bought my first ad in American Showcase. Jobs started coming in that had more 0’s in the check and the art directors were giving up to 2 weeks to finish work. This is when I really started to think that I could be a full time freelance illustrator.



















Was it tough to give up working on cartoons? That was sort of your soul for a long time.

I spent years in the cartoon trenches and I really loved it, but the moment to really plant a flag in that part of the field had passed. Maria, my high school sweetheart, landed a job at Channel 10 in Providence and we bought our first house. I always wanted to be a staff editorial cartoonist but that would have required taking a job in another city and Maria’s career was really taking off. Illustration work was starting to come in frequently and the money was better with each month.

Eventually the Boston Herald decided they didn’t need my work anymore, or couldn’t afford it. I don’t know which. No longer having the Herald as a safety net really gave me motivation (fear) to do better illustration work and become a better artist over all. I got pretty good with the airbrush and started experimenting with oils. I had absolutely no clue how to do what I was doing, and yet I stayed afloat. My ‘teachers’ by that time were the illustrators I was seeing on magazine covers and newspapers at the time. Mark Fredrickson, C.F. Payne, Anita Kunz, Tim O’Brien, Gary Kelley, Jack Unruh and more. There was a lot of really great work happening then.

Music has always been very inspiring to me as well. Even if it’s just the way a musician approaches the instrument. Steve Vai is such a virtuoso or how John Lee Hooker can say so much with one dry, dusty note. Ornette Coleman made me realize we don’t just go forward, backwards and sideways, we can go diagonally, do somersaults, make new shapes, just because we want to. Tom Waits showed me you could do any damn thing you please and as long as you’re doing it from the heart.







What's your medium(s) of choice?

Choice is the operative word, because these days there’s almost no choice. For illustration work digital is the way to go for me simply because I can draw, paint, make changes and send the final all in one environment. It’s cost effective time wise and materially speaking as well. 

Do you have a preference?

I always prefer the look of traditional to digital, at least when it comes to my work. I’ve been having an on again off again affair with oils for many years, but I’m committing to making it a bigger part of my life because it can be so beautiful. I’m in the process of reintroducing more hand made pieces and I’m excited about the possibilities. The only work I’ve had accepted into juried shows in the last few years have been either charcoal or oil paintings, so I think that’s a bit of a hint.

What are the tools you use?

I usually sketch my thumbnails in pencil in a sketchbook. My sketchbook is definitely not a beautiful James Jean affair. It’s stick men, scribbled notes, half ideas, mostly mind clutter I need to put down so I can have a clean slate in my head and proceed. Once I get some ideas I like I’ll sketch them in the computer (a maxed out Apple Mac Pro) on my monster truck Cintiq 27HD monitor in Sketchbook Pro or Photoshop. I’ll paint the final in Photoshop, mostly with Kyle’s brushes. They’re really incredible. For reference I shoot on my aging Canon 50D or my iphone. I back up to a 3TB Apple Time Capsule. There should probably be more redundancy in my backups. I saw yours, it looks like a backup disc version of a Marshall stack. I’m running with the devil.







Remind me, you didn't go to school for art, right? Did you go to college for anything?

Nope. Nuthin’. I was really stubborn about wanting to do the music thing. Practiced a minimum of 8 hours a day, sometimes 12. I wouldn’t even take the guitar off to go to the bathroom. It’s a big regret now.

Why is this a regret? Do you think there was something you could've learned in college that gave you more now than what you have?

It's a regret because my children have a father who is intelligent but under educated. My parents have a kid who didn't take advantage of opportunities they offered. I'm a man in his 50's who is limited in his professional opportunities because of the impulsive choices of an 18-year-old kid. I've spent a lot of time alone in a room alone trying to figure out how the hell to do what we do. Having someone guiding me would have saved me years. 







One of the defining characteristics that I think about when I see you is that you convey such an enormous love to your family. I mean, everything has its ups and downs but when I see you and your family interact, I can't help see the love between you guys. When you comment about not having degrees because maybe you're not a good enough Dad or Son, I don't think you're giving yourself enough credit - but I understand where that comes from.

You're obviously supportive of Maria and your kids. Knowing what we know about being an illustrator, how are they with that? I've had relationships in which I was broken up with because I was still in that precarious position of building an illustration career and they were afraid about the ‘money thing’. You've been with Maria a long time - how was it working those things out?

It makes me very happy that you see a loving family here. That’s our priority.

Maria has always been my biggest supporter and champion. Always. And I’ve always been hers. When we were starting out we both realized that we had chosen paths that had a high rate of failure. There have been times when one of us would look at the other and say: “I don’t know if I can do this”. The answer would always be “You can absolutely do this!” But you have a good perspective on how precarious it can be when you’re in businesses like ours.

Sometimes the wind is howling and you’re smashing through the waves, and then the next thing you know it’s dead calm and there’s no movement and you have to start rowing. You have to be with a person who can take that kind of pendulum swing. It’s not for everyone. I sometimes feel that even though I’ve been making a living as an artist for over 30 years I haven’t had a career as much as I’ve strung together a series of busy periods and survived the slow times in between.

That’s a great way to put it.

Thinking more about the college thing, I’ve learned more on my own than I would have been prepared to take in when I was 18. The fear of appearing uneducated has always given me motivation to keep learning. I think what I missed out on was meeting people, or even one person who could have steered me in the right direction, or shown me that it’s possible to do things I hadn’t even thought of. When I say I regret not going to college I mean that I’d like the freedom of options that a degree provides.

Also, I’m a 51 year old man commenting on the actions of an 18 year old. I’m pretty sure I’ll go back to school after we get our kids through their college years.







You've been doing this a long time and made it up as you went along. What experience as an illustrator was your most 'teachable moment'? You know, that time you really fucked up and keep in your head of 'what not to do'?

The one that jumps out for me is the first time I was hired by my favorite magazine while I was growing up to do a portrait of an iconic musician. As the sketch process progressed there were many notes and suggestions. They wanted to see in progress shots as I painted, which I thought was a bit much, but this being a bucket list job at the time, I acquiesced. With each shot I sent, I received very specific suggestions in return, to the point where I felt like I was doing someone else’s work style. 

At one point I even half jokingly wrote back to the art director “This looks like (illustrator’s name)’s work. Are you sure you don’t want him to do it?” The AD said no, do your thing, but the heavy-handed art direction continued. By the time I was done I felt empty. 

I felt that I had been art directed into aping someone’s style for some reason and because I was so excited about a big time gig I didn’t have the courage or, at the time, the integrity to stand up for myself and draw a line, so to speak. It felt like I participated in an exploitation of me and another illustrator whom I admired. I should have been proud of that job.

Karma being what it is, the illustrator who they should have hired saw the piece and called me out. It caused some serious social headaches for me. I’m grateful that we’ve become close friends since then.

What I learned is that if you catch a whiff of your integrity burning, pay attention and go the other way.













So. You were sitting at the drafting table and felt you needed some exercise. You started jogging and eating healthy eventually finding yourself doing a 5K then a marathon then an Iron Man....what the fuck Dale?! When and how did fitness become such a huge part of your life?

It became important very early on. Both of my parents were great athletes. My father briefly held a world record in swimming (a guy in the next heat beat his time) and my mother was a national champion swimmer in her teens. Before I was old enough or a good enough swimmer to join their practices, I’d be on the bench drawing. So both of these pursuits started very early.

I had a pretty successful run through high school as a swimmer and it ended when I decided not to go to college. In my late 20’s, I got involved in racing mountain bikes, which was thrilling. That evolved into riding and racing road bikes. I’ve always ran as well, having done a few marathons and half marathons.

A few years ago I decided to put all three together and try some triathlons. Of course it would make sense to start small, but the first one I signed up for was a Half Ironman distance race (1.2 mile swim, 56 mile bike, 13.1 mile run).

At that first triathlon, I beat the entire field in the swim, pros included. That’s after not swimming with any purpose for about 30 years! I was undefeated in my division and qualified for the Half Ironman World Championships as well as Ironman Hawaii, which is the full distance World Championship. I had a very good shot at winning the Half Ironman worlds last year. Unfortunately, on my last training ride before I was about to leave for Canada I was struck head on by a car and dragged for a little bit. As soon as I came to a stop I thought “Well, that’s over”.

One of the things I love about racing is that there’s a binary outcome. Win or lose. You can see by the numbers if you performed well. With art and illustration it’s amorphous. The quality of your performance is subject to judgment. It’s nice to live in both worlds and to not have to live in both worlds all the time.







I know the Boston Marathon a few years ago shook you up. I know you were running it and I was watching the whole thing go down on TV. It was horrifying sitting in my living room. You had just crossed the finish line about a minute or two before the explosions - and I recall you telling me that Maria and your kids had just left the precise location where one of the bombs went off closest to the finish line. The location they mostly show on TV.

It was an unforgettable day, very difficult to digest, even now. The whole ‘Boston Strong’ thing, I appreciate the sentiment, but being in the thick of that sort of thing you really don’t feel all that strong. You feel very vulnerable. You feel like the people you love are suddenly at risk because they came out to watch you play. It’s a complicated swirl of emotions and feelings that, for me, aren’t summed up in the Boston Strong slogan. “Still Here”, maybe?

In all, the way the region responded made me proud. New Englanders, and Bostonians in particular, can be a cantankerous bunch. It was heartening to see the Boston family pull together.

Aside from the sight of the bombs exploding my takeaway image was that of my daughter, Bella. Her hand in mine, nervous with sweat and wringing, eyes dark, quietly saying over and over “We have to get out of here. We have to get out of here.” with the Hancock tower looming behind her. I looked up at it thinking about what it would be like for all that glass to come raining down.

I think it’s natural to take a look at your own life after being in such close proximity to people who lost their lives or whose lives were violently altered. However, I’ve always felt very fortunate and grateful for my situation in life so I’ve never taken good fortune or those around me for granted. I think not feeling as though I needed to make a change in life after being so close to such a horrible event was an unexpected gift on a very dark day.