
Today we’d like to introduce you to Dale Stephanos.
Dale, we’d love to hear your story and how you got to where you are today both personally and as an artist.
As a kid, drawing pictures of people was the easiest, most direct way for me to connect with my peers and adults. It would make them laugh, or impress them in some way, which always surprised me. I don’t think I had any unusual talent. Looking back now, I see that I was an approval junkie, and art was a convenient vehicle to that (disappointingly shallow) goal. As I grew into adulthood, the approval took the form of a paycheck, and before I knew it, I was a professional artist.
In the late 80’s I was a struggling musician, supporting myself with my art, freelancing as an editorial cartoonist for several newspapers. I was living on Beacon Hill with my beautiful girlfriend, making money as an artist, and playing in the clubs at night with my band. As the music dream started to fizzle I remember thinking how smart I was to have such a solid backup plan being a freelance artist. My parents must have been grinding their teeth.
I worked as a freelance editorial cartoonist for the Boston Herald for 13 years, during which time my work was reprinted in Newsweek, Time, The New York Times, LA Times, pretty much everywhere. I self-syndicated to about 30 papers across the country.
During this time, I was asked to create more realistic illustrations, and having no idea how to do that, I of course, said yes to every request. The Boston Phoenix was a regular client, and it served as a kind of farm league for me. I could try different things, soar to the heavens, fail spectacularly, move on, repeat. That really helped me to build the art making and conceptual muscles it would take to succeed on assignments from the big national magazines like Golf Digest, Newsweek, Sports Illustrated, Rolling Stone, and of course, my dream job, the cover of MAD magazine.
I’m currently working on an item that’s high on my bucket list, a stamp for the US Postal Service.
We’d love to hear more about your art. What do you do you do and why and what do you hope others will take away from your work?
For my illustration work, I’ve created art digitally for the past 12 or so years. I work on a big Wacom Cintiq monitor that’s just like drawing or painting on a drawing table. It’s efficient, but a bit unsatisfying at the end, because you don’t have a physical, handmade object. About three years ago I started painting again. I missed being someone who makes things. In the process, I’ve discovered that people like buying paintings.
I’ve always believed that humor is the fastest route across any divide. My work has always had an element of humor in it. Today, I’m much more reserved in my approach. The humor is still in there but it’s not the most important thing to me at this point.
The time we live in is so distracted. I find myself wanting to make work that will make viewers want to pause for moment, look deeper. Portraits have been my bread and butter since the beginning. For me, there’s nothing better than being able to take a blank space and fill it with someone looking back at you. It’s fun to think of where this image will go, who will see it, who it would be seeing if it was sentient.
What do you know now that you wished you had learned earlier?
My advice for artists of any kind is to try to be comfortable with being a little uncomfortable. I don’t necessarily mean financially, but creatively. In exercise, you can’t grow muscles unless you break the muscle down first, then it repairs itself and grows, given proper nutrition. It’s similar with art. If you’re not filling up your head with new, challenging things, you’ll eventually find yourself out of ideas, and at best, repeating yourself.
If I could go back and advise my younger self, I’d tell him to evict the negative self-talker from his head, and to get out and network more. And wear nicer shoes for god’s sake. My future self would probably advise me to be more active on Instagram and Twitter.
Do you have any events or exhibitions coming up? Where would one go to see more of your work? How can people support you and your artwork?
I have about a dozen or so large giclees for sale at the Jordan’s Furniture store in Reading, MA. Eliot Tatleman was very generous to allow me to try some things in that spot.
My paintings are shown regularly at the Next-Door Gallery, in Mansfield, MA. I had a pop-up gallery on Newbury Street this past December. It was fun, and I learned quite a bit. I’d like to do that again. I’m looking for a good spot on Martha’s Vineyard to try a pop-up gallery next summer. I always have hand embellished giclee prints for sale on my website, www.dalestephanos.com. I also take on private commissions.
Contact Info:
- Website: www.dalestephanos.com
- Phone: 6176971343
- Email: dale@dalestephanos.com
- Instagram: https://www.instagram.com/dalestephanos/
- Facebook: https://www.facebook.com/dale.stephanos
- Twitter: https://www.instagram.com/dalestephanos/


Prince, 11/15/16, 12:32 PM, 8C, 5350×9759 (648+643), 100%, Art 1, 1/40 s, R119.0, G88.5, B100.5


Image Credit:
©Dale Stephanos 2018
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