Q&A: Illustrator Jack Dylan preps for the Drake Spring Market


Hailing from Montreal but now happily entrenched in Toronto’s Trinity Bellwoods neighbourhood, Jack Dylan is an illustrator whose work has graced the pages of Toronto Life, The Walrus, Maclean’s and The Globe and Mail. Best known for poster art reminiscent of what you’ll find on the cover of The New Yorker on any given week, Dylan’s wares are on display this weekend at the annual Outdoor Drake Spring Market. Alongside handmade jewellery, one-of-a-kind art pieces and vintage furniture, Dylan’s posters depicting the Trinity Bellwood’s gate and a Mount Royal beach scene are up for grabs.

If you’ve ever wondered what went on inside the head of a talented illustrator with a penchant for podcasts and sandwiches, look no further. We cornered the busy artist recently and asked him about the most scathing criticism he’s ever gotten and his favourite place in the city to put pencil to paper.

Having moved to Montreal to Toronto, would you say your illustrations have changed in any way?

It has, though I’m not sure if that’s due to the city, and not to something more natural. — I will say that I think about Design a lot more than I used to, and that’s had a big influence on my work. Toronto is a big design city, it loves all design, and there are so many talented designers here who put attention into everything, so that’s very inspiring. Montreal, the Mile End neighborhood where I lived, it’s not really like that as much. It’s aesthetic is a little more casual, a little more messy and not at all glossy, and that’s on purpose. So it’s exciting to be in a place were people are very dedicated to the design of everything. It’s got me thinking that there’s a lot more I’d like to do.

What is the process of creating your art like?

I tend to work best in blocks, so I like to clear a few days for any project and just keep focused. I’ll start with sketches on scrap paper, surf around Google images and create mood boards. Then I’ll scan a rough pen drawing and start tracing over it in Photoshop.  In between I take power naps, and buy sandwiches. During a medium sized piece I’ll listen to around 5 to 10 hours of podcasts.

Where do you find inspiration?

I’m very lucky that I get to work from home and have the freedom to slack off now and then, because it really comes in handy when I need to get ideas. I like to take walks a lot and just look around and think. My personal work draws a lot from the city and day-to-day life, so I’m always looking for something that inspires me. Today I saw a woman in a beautiful business suit, with her hair pulled back. She looked like she was on her way to a law firm but she was carrying two cat carriers like brief cases, and she had her daughter with her. Her daughter’s coat was white with big colourful polka dots and was in total contrast to her Mother’s grey jacket and skirt. That really stood out to me. I like the moments of uniqueness and color in everyday life.

How would you describe your art stylistically?

Lately I’ve been using the word “modernistic” because I’ve been using a more historically influenced style. It’s inspired by poster and cover design from the 1920’s – 40’s, because that (I feel) was really the golden age of illustration in print, and that’s what I try to recapture in my work. I think my style has become about colour, pattern and design, and I’ve started constructing images with shapes and collage, almost as much as I draw them the conventional way. So it’s very “modern” in that sense, in that my images are slightly abstracted and mechanically made, and draw upon a specific tradition. Sometimes I call it “romantic modernism” but that’s maybe a bit too heady.

What’s your favorite medium? Why?

I’m very interested in Art Deco, and those stylistic techniques all fit in very nicely with PhotoShop, where you can easily use straight lines and shape tools to construct images. It’s a little hard to believe, because I started out as a painter. But now I really like making an entire piece on the computer, partly I think because I’m not always creating a giant mess and having to hunt for misplaced tools all the time.

Why are you drawn to poster art?

As a working artist I discovered that poster was a great venue for art to express itself, because it’s public and because it’s constantly in demand, with a new poster job always just around the corner. So it’s an amazing platform for the artist to experiment and be inventive with. Before that though I also always loved poster, because I truly believe that there you have some of the most beautiful works of art. Art Nouveau, Art Deco, Magazine and Comic Book covers all spoke to me as much or more than other images in “Fine Art” because in poster the art is always intended to deliver a message or tell a story. And I loved that an image could be both beautiful and narrative. Yet poster is always just hinting at a larger story, which is I think, what makes it so enticing.

Where is your favorite place in the city to work?

Just my studio on Gore Vale, which faces Trinity Bellwood’s. There I can always walk in the park if I need a break, or people watch.

Who are some artists you admire?

Too many to tell. But I think everyone should know the names Adrian Tomine,  Chris Ware, and Jillian Tomaki. Their work in contemporary illustration has been so amazing, combining aesthetic design and story telling in ways that are just so impressive. Some of my historical influences are the poster and cover artists A.M. Cassandra, and Joseph Binder, and the hundreds of amazing illustrators who’ve worked for The New Yorker over it’s history.

Do you remember the first piece of art you ever created? What was it?

Yes. It is was actually in fashion of all things, as a milliner; designing bowler hats out of construction paper for my cat Casey. I was three, and a failed hat often ended in tears.

If money nor time was an object, what’s an art project you’d undertake?

Actually I would love to design a house, or municipal building like a library, or a public park. Creating a real environment that people could actually inhabit, instead of just drawing one, would actually be a big thrill. But on the more realistic side of things, a children’s book, or a graphic novel.

What’s the most flattering compliment you’ve ever gotten for your art? 

I think when Joanna Newsom (an American harpist, pianist and songwriter) stole a bunch of the posters from the venue, and then got a manager to ask me for more. That was a nice moment.

What’s the most unflattering critique you’ve ever gotten?

Those all probably came from myself, which is a good or bad thing depending on how you view it.

What piece of art are you most proud of? Why?

I think right now, my “Trinity Bellwoods” piece.  I know that it’s one that resonates with a lot of people in the neighbourhood, and it’s great to feel like something you’ve created will be held onto like that.

Why are events like the Drake’s Spring Market so important for up and coming artists?

For me, as an illustrator — which is an isolating job — markets like the Drake’s have been a very important way for me to get my work out there, and meet face to face with people who know it. Often people are surprised to meet me, or that I’m “the guy who created all those posters.” And that’s very valuable because, a) After you’ve been working alone for months on something, It’s really nice to hear after that people actually like it. b) It’s a really important way to directly support works that otherwise would not get funded. Often my non-commercial work is what sells the best at markets such as the Drake’s, and if it weren’t for that revenue these works would earn very little.  So it was through these types of events that I was really able to start to create the kind of artwork I most wanted to produce.

The Outdoor Drake Spring Market happens this Saturday, April 3oth from 10 am to 4 pm at the corner of Queen St. W. and Beaconsfield Ave. Come early to get first pick of the Drake General Store’s sale stock. For more information, click here.

Interview by Maria Cootauco. Illustrations courtesy of Jack Dylan.

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