Inside Out’s Own Curt Montgomery on His Minimalist Style, Insta Fame, and Almost Going Broke

Curt Montgomery
Credit: Sarah Harvey

Above all else, Curt Montgomery—the Toronto-based tattoo artist whose bold, minimal style has led him to ink the likes of Halsey, Joe Jonas, and Sophie Turner—is a good Canadian boy. The 38-year-old hockey fanatic (he grew up with dreams of playing in the NHL and is fluent in hockey slang), frequenter of Tim Hortons, and lover of B-rated Canadian television shows like Corner Gas and Murdoch Mysteries, began tattooing later in life after stints at various, often random jobs, but over the past four years his career as an artist has truly taken off.

Becoming a tattooer was never exactly an aspiration for Montgomery; it wasn’t something he seriously considered until briefly working as a receptionist at a tattoo studio when he was in his mid-twenties. Now, over a decade later, he’s bona fide Instagram famous—although you’ll never hear him brag about it—having racked up nearly half a million followers in just a few years of tattooing. If you look up ‘minimal tattoos’ on Google or Pinterest, you won’t be scrolling long before you come across a piece of his. Chances are, in fact, that you’ll find one on the first page.

“Everywhere you look now, you see the style of tattoos that I do, but that wasn’t true when I started doing this a few years ago,” the resident artist at our very own Inside Out studio says. “At the time, the minimal style was new to Toronto, and to most of Canada even, but it was a trend people liked so, thanks to Instagram, I started to catch fire quickly.” Montgomery credits a lot of his early success to Instagram. His signature hyper-sexual imagery helped him stand out on the budding social media platform and build a large roster of both clients and fans.

Love his cool, minimal style? You can shop Montgomery’s tattoos in semi-permanent form via his Inkbox collection here.

But before success came rushing, there was a time not long ago, in mid-2015, when Montgomery could barely make his rent. He recalls being short $500 one day before his monthly payment was due. In a bind, he called his mother and asked her if she’d be willing to help him out. She was, and incredibly grateful, he told her that if his appointment later that day went well he’d likely never need to ask for this kind of help again. He was right. A few hours later, he tattooed Halsey for the first time. “There have been very few days since then that I haven’t done a tattoo.”

I first met Montgomery in August of 2017 for a tattoo appointment of my own and noticed that he seems, at least from the outside looking in, to live a relatively simple, solitary life. He arrives at work at eight o’clock in the morning each day to draw, tattoos throughout the afternoon and evening, and typically ends the day with training (he’s currently doing a mix of strength training, yoga, and hockey/skating drills). To interview him for this article in particular, we met up for a very late dinner (we sat down to eat at 10:30 PM) at a local staple—The Thompson Diner—right after his Wednesday night yoga class, because late night is when his free time begins.

His half of a tattoo trade between Montgomery and fellow artist Mira Mariah (@girlknewyork), done during her guest spot at Inside Out studio

In many ways, Montgomery is a simple man. He clearly values balance—grilled cheese and fries with chicken noodle soup after yoga, and days of high stimulation, tattooing while chatting with clients, paired with nights spent drawing or watching TV with his dog Peanut. But he is also staggeringly complex. Three times over the course of his adult life, at various inflection points when he was unsure what to do next, he fled to remote Northern Ontario for anywhere from six months to a year to draw and be alone with himself. Even his Instagram bio, which reads “Tattoo Artist = Honey Badger Hero” and to an onlooker just sounds like an inside joke, is surprisingly deep. “Look up ‘honey badger’ on YouTube,” he instructs me, “it’s a video of this tiny animal that punches above its weight, continually gets hurt, but comes out winning.” For the record, this is the video he’s referencing, and the honey badger, he explains, is an animal that reminds him of himself during his early days as a tattoo artist.

While it can be easy to assume that someone with such a large number of fans, celebrity clientele, and an aesthetic that continues to gain popularity might come off as cold, aloof, or even mean—something many tattoo artists are accused of by clients craving a more comfortable experience—in Montgomery’s case, that assumption is wrong. Asked if his laid back, kind personality ever surprises people, he admits it does. “Three people have commented on it just this week. They say that I don’t look like the way they thought I’d look or that I’m nicer than they expected, and to be honest, I like for people to be underwhelmed by me. If you’re overwhelmed by or uncomfortable around your tattoo artist, your experience isn’t going to be as enjoyable, so when I’m tattooing, one of my main goals is to give off an aura of calmness.”

One of the ways he achieves this calm, collected mental state is through a pre-tattooing ritual; something he’s adopted from his days playing competitive sports as a child. “I set my station the same way before every single appointment,” he says, “I take a moment to myself, stare at my station, grab a piece of gum, put essential oil on my wrist and rub it in three times, put my glasses on backward, and then I can start tattooing, but during that short chunk of time I can’t speak to anyone. It’s exactly how I was before playing a hockey or lacrosse game when I was growing up; I wouldn’t speak to anybody all day—not at school, not at supper. That minute, whether it’s before a game or a tattoo, is important to me, and when it’s done I know that I’m ready to go.”

Montgomery belongs to a growing number of tattooers who were artists first. Although tattooing isn’t the career he imagined for himself—granted there was no career he imagined for himself— art, on the other hand, is something he’s been working on throughout his entire life. In high school, he participated in an advanced art program for a while but dropped out to focus on sports. He always enjoyed illustrating, but only did it for fun until age 22 when he gave up drinking (he’s been sober ever since), moved into a tiny apartment behind a restaurant, and took a job as a farm hand working at a flour mill.

“Because I quit drinking, I needed a new hobby, and it was drawing. I would draw all the time. For eight months of my life I would go to bed at 10:30 PM, wake up at 3 AM and draw until 5 AM, then go to the flour mill and work from 7 AM to 3 PM, come home and nap until around 5:30 PM, and then draw from 6 PM until I went to sleep.”

Following years of intense practice, two more forays into Northern Ontario to focus on illustrating, and a few art school classes (he dropped out after a year), Montgomery noticed that his art was steadily improving. He landed a couple of contracts as an illustrator and after a while, at the urging of a former girlfriend, he decided to put together a portfolio of drawings, bite the bullet, and get a tattoo apprenticeship—it just felt like the logical next step for him. Because he knew some tattooers from his previous job working at a studio, he had friends to vet his portfolio before he officially applied anywhere. Having that feedback helped, and the first shop he showed his drawings to hired him on the spot.

After trying his hand at tattooing the hyper-realistic style he was accustomed to illustrating, Montgomery realized that what he most enjoyed doing was what is now his signature bold, minimal imagery inspired by the Russian Criminal Tattoo Encyclopaedia, a book published in 2004 that features small, simple black line tattoos (including the kinds of skulls and hands that frequently appear in his designs). This style has led to opportunities far beyond tattoos for the artist, who, this past year alone, has worked with The Annex Hotel on its branding, released a limited edition jewelry collection with For Love Or Money, and, most notably, illustrated a forthcoming book of poetry written by actress Lili Reinhart. Although tattooing isn’t necessarily where he imagined himself, it’s been the key to his success to date—something he doesn’t take for granted and the reason he’s so openly grateful to the clients who put their trust in him and his art each day.

If you liked our profile on Inside Out’s resident artist Curt Montgomery, make sure to check out our profile on guest artist Mira Mariah here.

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