Possessing a love, talent, and dedication to his craft shared only among the truly elite, Timmy Sneaks is quietly emerging as perhaps the best pop artist in the game.

Cover by Danny Direct

Surely most people who drive by the Boston artist studio, with a dog bed set up in the corner, wouldn’t expect that within its walls works, day and night, a pop artist who’s been called by Influencive “the artist of a generation,” who’s created custom pieces for Rob Kardashian, Scott Disick, DJ Khaled, Post Malone, and Tdot Illdude, who name-dropped him in one of his singles, calling him “the next Picasso.”

But then again, Malden-born and North Shore raised Timmy Sneaks, has never been quite like what people would expect from him – and he has never cared much what they thought either.

Most people with those accolades do, at some point, start to believe their own hype.  “I still question if I’m good at it,” he says.

He’s lived his life in constant pursuit of mastering the different modalities of art: sketching in his school notebooks in between taking notes, tattooing, painting, sculpting.  Although he has an underlying confidence in his ability, it’s not some relentless drive to be the best.  Timmy Sneaks just loves what he does, and would rather do that than just about anything else.

Image by Gabby Baglieri

The only thing on par with art for Timmy is spending time with his family, who have been a part of his entire journey.  His parents’ journey has shaped his; they’ve combined stability with an entrepreneurial spirit.  His mother, Sandra, owned and operated the ABC Nursery & Day Care Center preschool in Malden; and his father, Rich, is the executive director of elementary education for Weymouth Public Schools. He has previously moonlighted as the owner of Fizz Ed’s sports bar -also in Malden- and, more recently, was added to Timmy’s management team. “I got there by default, I think,” is how Rich describes it.

Whether it was athletics or art, family was always there to support him.  He often chose to express himself with dyed hair and baggy clothes; they never tried to get him to change or conform, and he never wondered or cared what anyone else thought about his style.  As Timmy moved up the youth hockey ranks, Rich, who ran the program at Malden High for years, was his coach.  “You go on a lot of long car rides and there’s a lot of conversation.  We’ve always been really close.”

If Timmy still wonders if he’s a good artist, he surely will never be caught bragging about his hockey days, but those who watched him play growing up insist he was good at that too – good enough to be on some travel teams with Jimmy Hayes.  Regardless, Rich could tell that Timmy’s passion was art.  By the time he was in high school, that was clear.

Image by Gabby Baglieri

“He said ‘I want to be an artist.” I said ‘you want to be….what?’”  Rich didn’t know anything about the art world, but he knew his son.  “I always knew, when he gets focused on something, he’s gonna be ultra-focused.  When he’s locked in and he’s focused, he’s just not gonna take no for an answer.  I want him to do what he wants to do, and I’m always there to help.”

For Timmy, on some level he always knew this was the path he wanted to take.  “I think very early on,” he says.  “I had always grown up drawing and painting.  As far back as I can remember, I definitely knew this was what I wanted to do in some capacity.  I just knew that I wanted it more when it came to art.”

His mom still has those school notebooks, covered in drawings. “There’s this mantra of ‘you’ll never make it as an artist,’ it’s this looked-down-upon thing.”  But when the time to consider and apply for college admissions approached, Timmy’s list of schools only included those with exceptional art programs.

His parents were all in; his well-meaning guidance counselors tried to steer him towards a more traditional route, just in case.  Timmy wouldn’t hear of it.  “I didn’t want a backup plan, I wanted to do whatever I had to do to make this work.”

Image by Gabby Baglieri

He chose to attend the Savannah College of Art & Design (SCAD).  By then, he had also begun looking into working as a tattoo artist apprentice.  “Early on, I was super into stuff like tattoo aesthetic and skateboards, street art kind of stuff.  I was so intrigued by them.”  This is when he began to work under the name of Timmy Sneaks, a childhood nickname inspired by the movie “Goodfellas” that stuck.

Two weeks before he planned to return to Savannah for his junior year of college, a friend with a tattoo shop in Massachusetts reached out to him, offering him a spot as an apprentice.  He really wanted to do it; his only reservation was whether or not his parents would be cool with the idea as well.  Typical them, of course they were, and for two years he worked diligently at the shop, perfecting his craft.

The money earned would be put towards his art supplies.  Friends would ask him to draw designs for them; so did his sister, Briana, a fellow entrepreneur and  owner of “The Groom Room,” a dog grooming service in Reading.  “I would always ask him to draw tattoos on my arms with markers until we were bored and now I wear his art permanently.”  At first his parents were skeptical of all of the new ink; the whole family has tattoos by now.

Image by Gabby Baglieri

After finishing his apprenticeship, Timmy went back to SCAD, having promised his parents he would finish school.  While he worked towards his degree, he also tattooed at a shop in Savannah.  “Art school definitely taught me discipline,” he says.  “People who have never gone to art school don’t realize how intense it actually is.  It’s all about deadlines.”

Once he returned, his passion for painting grew.  Timmy took full advantage of SCAD’s facilities, and spent most of his free time there, completing his projects and honing his skills trying new things and experimenting with different materials.  His parents would come visit on the weekends.  “We would have more fun than he did,” says Rich.  “We would go out and have a good time.  He was all business.”

After graduating in 2013, Timmy returned to Massachusetts to work in a tattoo shop where he was already established.  He continued to experiment and paint, saving the money he made tattooing for whatever the next step was, not sure of what it would be but continuing to push himself to be ready for wherever opportunities came his way.  He enjoyed tattooing, though not the aspect of dealing with people, and after having done it for a while he wanted more.

Around that time is when Timmy stumbled upon an article that he still has saved in his phone; the article that changed his life.  It was about artists featuring their work at the Art Basel annual show in Miami Beach, and celebrities buying millions of dollars’ worth of art at it.  But unlike what you’d expect, it wasn’t Art Basel and all that comes with it necessarily that caught his eye and drew his inspiration into the target of his laser focus.  It was the mention of the name of one of his favorite artists, Frank Stella.  Like Timmy, Frank, was also born in Malden.

Image by Gabby Baglieri

“I just believe in weird, crazy shit like that,” he says.  After reading the article, Timmy decided to leave tattooing and give himself one year to get to Art Basel for the following year’s show.  He knew nothing about how Art Basel worked, but knew that painting would somehow be his in.

“This just seemed like the place where I should go if I want to do this,” he said.  He didn’t know what he didn’t know about preparing for Art Basel, and quickly found out that not only did the booths cost at least $10,000, all the booths for the next show had been booked months in advance, basically since the last one had ended.  He’d reached out to the curators, who’d told him they liked his work but he would have to try for the following year.

“I was kind of down about that,” admits Timmy, who had put all his eggs in that basket.  “But randomly, about two weeks later, one of the shows reached out and said ‘hey, we just had somebody cancel.  It’s one booth.  Do you want it?’”  Believing it was fate that everything fell together, he readily took it and poured his savings from tattooing into it, viewing it as a career investment.

It paid off.  Naturally Rich, Sandra and the rest of the newly formed management team, came to Art Basel with Timmy, nailing his pieces to the tiny booth walls themselves.  “When I saw people lining up to meet him and shake his hand,” said Rich, “I said to my wife, ‘I think this art thing is gonna work out for him.’”  He sold much of what he’d brought to Miami, and began to create some buzz for himself in the industry with his pop art standing out among the different styles that were featured that year.  “I think for me, it was talking to people and the reactions I was getting, and the people I was meeting.  It basically sort of legitimized it to me that maybe people would be interested in this.”

Image by Gabby Baglieri

It wasn’t just that though.  “Every time you think this thing is gonna be the thing that changes everything, it never is.  It’s always an accumulation of things,” he explains.

One of those things was Instagram just starting to become the biggest social media platform in modern society.  When Timmy saw it, he knew it was a game-changer for the art world.  “You have a gallery in your pocket now.  It was just so visual, and every person could now be their own brand.”  He embraced that grind of learning how to master the platform’s nuances to create content and build his following.  At Art Basel, he’d met prominent gallery owners, but saw that social media – without a middleman – was the future and a more direct route.

“I was really sleeping and breathing this thing that I just felt like I had to do,” he says.  “I was mostly spending my time in the studio.” He was also doing digital art, like t-shirt designs, recognizing the market for it in the digital era. It was beginning to take off, but wasn’t really recognized as “fine art.”

“I made a conscious decision and said ‘how can I take this digital aesthetic and turn it into a style I can paint with?”  The combination of digital art and painting, influenced by his tattooing background, became the style that Timmy Sneaks has become known for – making things look machine-made without being machine made, and bringing clean lines to the more raw form of street art – and has caught the eye of some of the world’s most famous entertainers.  One of the first to recognize his work was Rob Kardashian, who had received one of his pieces as a gift and posted it to his Instagram page.

“That was the first time that my Instagram was crazy after that.  All the sudden, I had thousands of new followers overnight.  That was a weird experience because that was the first time that had happened,” he reflects.

Image by Gabby Baglieri

The next was when he did a custom piece for NBA player Patrick Patterson, then playing with the Toronto Raptors.  Timmy drove it to Toronto to hand-deliver himself, and attended a Raptors game. “That was another moment where I was like ‘this is cool that I get to do this kind of stuff because of making art.’”

The Instagram content creation became almost like another full-time job; when answering e-mails and corresponding with people got to be too much, Timmy knew he ultimately needed to expand his circle, although he didn’t want to hand off these growing details to just anyone.

“I’m a bit of a control freak,” Timmy admits. So with careful vetting, and of course some valuable input from his family, key additions were made to the management team.

Family is just as important to Timmy as his art; he has spent most of his adult life in the Boston area, staying close to them.  He spent time living in Los Angeles; the weather was certainly better, he says, but he also understood that in the digital world we live in, he never had to be in a certain place to be successful.

Of course, his father is a part of his professional life and his parents have always been his biggest supporters, but he involves his family in just about everything he does.  “He’s my best friend and always has been,” says sister Briana.  “He’s taken his art all over the country and it’s been so awesome to travel with him to see all his shows.”

Image by Gabby Baglieri

His cousin Gabby Baglieri is an accomplished photographer, and true to the family dynamics Timmy’s most trusted and consistent collaborator.

“Photographing Timmy is a very unique experience to photographing anyone else.  Once the ideas start flowing between us it’s like we have to stop everything and rush to make the art come to life,” Gabby says.  “He never says no to any crazy idea I come up with.  We have a very symbiotic relationship when it comes to creating content and have grown so much together over the years.  I’m super grateful for the opportunities we’ve gotten to experience together.”

His work might be ingrained in “the scene,” and he might pop in every now and then, but truly what Timmy enjoys most is being in the studio, pushing himself, mastering skills, wanting more, starting all over again with new ones, and combining them all to create something new.

“I’ve always been a little bit of a homebody, or mostly in the studio,” he says.

That studio time was further heightened over the last couple of years as Boston, along with the rest of the world, adjusted to pandemic induced restrictions and isolation. While these conditions hampered many globally, Timmy -as he has always done- focused on the opportunities in front of him, continuing to expand his craft. This culminated last summer with his first solo art show at Pellas Gallery on Newbury Street from May 14th to July 1st.

Image by Gabby Baglieri

Not surprisingly, the show and the Timmy Sneaks collections were a resounding hit at the gallery during this six week exhibit.  Owners Alfredo Pellas and his fiancé Isabel Arguello, have developed a strong chemistry with Timmy and an encore collaboration show is being planned this summer in July.

“Working with Timmy has been truly incredible. When I first met Timmy I saw the potential and offered him a solo show right away, something I rarely ever do. I do not think it is a coincidence that he is from the same little town of Malden as the great Frank Stella, and I think he will likewise rise to greatness,” says Pellas when asked about their gallery/artist connection.

“You should know that Timmy has no artist assistants, he does everything himself even the woodwork and cutting of his sculptures,” Pellas continues. “A rule of trade that Rachel Lehmann taught me is that a gallerist should never work with a lazy artist, no matter how talented he/she is, and let me tell you Timmy is the opposite of lazy. His dedication and focus on his craft is on another level. He is consistently innovating his practice, investing in new machinery new tools to make sculptural paintings. We have sold several dozen of his works and every time he brings something to the gallery its more refined than the last. He’s really what you search for in an artist, always pushing the limits, refining and honing his craft yet maintaining that power where you can see any of his works and immediately say ‘That’s a Timmy Sneaks piece.’ My father and I have collected several of his works and will keep on collecting. We are really proud to be his lead gallery and will always do our best to catapult him to new heights.”

Image by Gabby Baglieri

It’s 4pm on a sunny spring afternoon at Timmy’s brand new studio in Boston. Danny Direct is wrapping up the final shots of the spring cover shoot for this magazine. Rich, still in his school administrator attire from his day job, is keeping Timmy on a tight schedule.

The Celtics have just swept the Brooklyn Nets out of the first round of the NBA playoffs and the team has returned to Boston. To celebrate the sweep, Celtics forward Grant Williams has purchased a custom piece from Timmy, to be hand-delivered for 5pm by Timmy himself. A deal that Alfredo Pellas, and Pellas Gallery, helped put together with the Celtics big man.

Upon hearing this, BostonMan publisher Matt Ribaudo can’t help but ask, “Did (Grant) have you create a Batman piece for him?” referencing the superhero nickname Williams is becoming known as throughout Boston.

“No, not this time,” Timmy says. He pauses briefly and then adds, “But that would be pretty cool though.”

You could say everything Timmy Sneaks is doing is “pretty cool.” His works are housed around the world and in homes of many top recording artists, movie stars, and professional athletes. He was named Boston’s top up and coming artist with New Era and New Era Europe. His custom art can be found all throughout Boston. He’s at Time Out Market in the Fenway consisting of a 40′ commissioned mural by Steve Samuels. He has a commissioned piece at Earl’s at the Prudential Building. There are pieces at The W Hotel, Yvonne’s Restaurant, Bijou Boston, The Card Vault (Big Night Boston) and the list goes on, only continuing to grow.

For Timmy though, he remains most at home spending time in the studio and with his family.

“Everything he has accomplished.. he remains so humble and modest,” Rich beams. “Sometimes he’ll get a little agitated with me for talking about his achievements, but hey someone has to do it.”

 A smile breaks out as Rich is speaking. It’s the smile a father has while discussing the accomplishments of his son. He momentarily stops, perhaps to process his next thoughts, or perhaps to reflect on all that has led to them. Then the smile grows wider and broadens across his face, “I guess you can say he is sneaking to the top.”

Image by Danny Direct