STOCKBRIDGE — American artist Maggie Mailer has been drawing inspiration from the undulating Berkshire Hills for much of her career. “Anyone who has lived in the Berkshires knows how beautiful it is, and there is comfort in that,” Mailer told The Edge in a recent phone interview.
Not that she’s one for sticking with what’s comfortable. Over the years, since moving from New York City to Lenox, the self-taught landscape artist has been thinking deeply about the way she engages with paint and the psychological resonance that comes from the process.
Her most recent project? Illustrating a clever children’s tale about a young boy who fights schoolyard bullies with his mind instead of his fists. “In A Pickle” by Martinko (Hat & Beard Press, 2021) is due out today; in it, Mailer’s nostalgic, vintage-looking illustrations bring this timeless new story to life for young readers. She shared insights into the book’s apropos title quandary; how she approached this, at times unconventional, collaboration; and ways in which the local landscape continues to influence her work.
Hannah Van Sickle: I have interviewed many writers, but few illustrators; what can you tell me about the process of illustrating another’s work: is there collaboration or is the work largely independent?
Maggie Mailer: It’s interesting to hear myself referred to as an illustrator because my background has been mostly in painting. I did illustrate one other book, in black and white, but this is my first full-scale, full-color book.

I really just tackled this the way I would tackle a painting: I jump in and don’t have a clear idea of how I will begin or end — I am just led by the process. In this case, I really liked the idea of working with the text because text has always been really close to home, having grown up in a literary family. It was something I used to bring into my studio practice; I would often read before I would paint — I was an English major — I really wanted language to get into the paintings. And then I would forget about what [I read] or wrote and start painting, and listen in a stream of consciousness way. So I think there was a thread of that process as I was working with this text. I did not work in a linear fashion; I started wherever was most alive on that day, and then I would jump around. It was constantly a surprise to myself.
HVS: Your work has been known to explore the overlap between play and diplomacy; where does this tendency stem from, and was this approach organic or intended to invite a more diverse audience?
MM: I think it’s both. It’s definitely organic, [as] I grew up with eight brothers and sisters from six different marriages — one father — so I didn’t think of it as diplomacy at the time, just navigating that family structure really deeply affected the way that I work and the way that I handle paint.
I am always interested in the way one idea overtakes another in the painting process, how it starts with a clear idea and inevitably something else wants to assert itself — again, a constant back and forth between different ideas. I started thinking about how that feels like diplomacy, or it feels like a geo-political move between terrain within a painting — trying to take my own process and map it on a much larger scale — without even having studied or been educated in any rigorous way. [I am] just trying to understand in a really human way: What is the connection between these needs to take over a territory within my own painting or within the psyche or within a set of ideas — the need for dominance and power? What does that look like?
The same thing is really happening on a global scale. I was really struck by the archetypal move, it happens on an individual level and it happens on a global level, this need to overtake something. A kind of familiarity with working and reworking something. I call that diplomacy.
HVS: From landscape paintings to roving installations, you work in varied media; how did you land on watercolors for the illustrations you created for “In A Pickle”?

MM: Watercolor is not a medium I had been using in any extended way in the past; it really just happened naturally. I was coming up with artists who I wanted to use as inspiration for the book and one of them was Marcel Dzama, who is one of my favorites — I am a big fan — and then there is a book from my childhood, “The Doyle Diary,” made by Sir Arthur Conan Doyle’s father, Charles Altamont Doyle. He had these really whimsical watercolors that felt sort of Victorian and really sort of otherworldly, beautiful with pen and ink. As a child, I used to try and copy those, and I did a lot of pen and ink growing up and just sort of abandoned it.
When I was starting to work on this book, that [medium] came alive again — it wasn’t really a choice; I found the materials, they found me, and I started collaborating with [them]. I really love the softness of the watercolor. I realized early on that, especially because we were also animating, that I would have to make a lot of changes quickly. So working with oil paints — my normal medium — or even acrylic paint, just felt too cumbersome. Watercolors are so fresh and immediate.
I also worked on the computer, in Photoshop, which was new for me. I was handing work in to the animator at the same time I was making images for the book. It actually became this dialogue with the digital world, and I was really interested in sewing together the soft, fluent world of the watercolor and the child, and allowing the voice of the computer and the digitized marks to sort of be the voice of the [adult] world the boy is entering. So there are little moments throughout the book that I make it very obvious that I used a computer — I cut off the edge of someone’s clothing, or [make visible] a computer-rendered moment in what’s an otherwise very painterly scene. It’s pretty subtle, but I wound up really having fun with that — a way to make fun with this medium that has now become such an intimate part of our lives, especially last year.
HVS: Tales of bullies are certainly timeless. This book, at this particular juncture in our fractured society, feels apropos — any thoughts on the auspicious timing?
MM: It really felt like a cosmic joke! When I was handed the story, back in 2018, I didn’t really think about [the title]. By the time we were actually working on the book, and we were in the middle of 2020 and everything that was going on — I was working for the entire year on this book, “in a pickle” — I just really had to laugh. It did seem like some sort of divine timing, [although] I don’t know how or why. It helped me to get through the year; it felt really great to have a project I could focus on in the midst of what felt like everything that I knew coming apart.

When I agreed to work on the project, I wasn’t really thinking about the bullies so much; there were other aspects of the story that spoke to me. And then, when I was midway, I started remembering times in my own life when I was bullied, and it [became] really dear to me to work on this project. The way in which I approached the bullies was to almost make them, on the one hand, recognizable as mean kids, and [on the other hand] they almost look like monsters. The book has this quality of being in the realm of myth — the storyline of the snakes, as heroes.
HVS: You call the Berkshires home; how has this particular landscape influenced your work, and how have you left your mark here?
MM: Place is just so important. For the time that I lived [and was painting] in New York, I was always somehow evoking the Berkshires; the mountains have always been a theme, and trees and landscape and foliage. The Berkshires are a layer that’s in the work; there is a kind of beauty [here] that, no matter how hard I try, winds up as a theme in the paintings I make — and I have sort of given up apologizing for it. [But] it’s not just about making beautiful images; [I strive for] cross currents that hopefully keep the work compelling.
The Storefront Artist Project … began when I was living in New York, [thinking] about breaking the forced wall of the studio and allowing the studio process to extend, to sort of allow the whole world to feel like a studio, rather than just one room. When I got to Pittsfield and saw all the empty storefronts, I put the two ideas together. [I thought] this could be really good for the city of Pittsfield, which was really struggling and had 25 empty storefronts. I began speaking with artists and landlords, and we all got together; we had this kind of temporary residency that lasted about 10 years. We formed a nonprofit, [and] that was a big part of my life, a big chapter. In some ways I didn’t want to leave a mark — I wanted the project to exist and then disappear — but it was an exciting time, and it’s great to see Pittsfield [today] with an incredible gallery, Archive/Project Space, and some really vibrant art life happening — that makes me happy.
Note: The book, currently available through Hat & Beard Press, is being adapted into a short animated film with Mailers’s illustrations, narrated by the legendary Peter Coyote. To give back during this time, a portion of proceeds from “In A Pickle” will be donated to Horizons National, whose programs close gaps of opportunity and access for students in under-resourced communities.