In a secluded alleyway off Pearl Street in Boulder, Colorado, street artist SMiLE is taking a can of spray paint to a giant patch of brick wall. I’m acting as his lookout, although it’s pretty clear he doesn’t trust me — he stops painting every few seconds to anxiously look over both shoulders. 

He insisted we meet here late at night, to avoid detection by the cops. He has an alibi planned, if the police start to interrogate us. He’s buried inside a tattered black hoodie, and jittering like a crack addict.

photo - native american  chief -  street art - colorado

[photo Samantha Keller]

When I tell him he’s being paranoid, he responds, “paranoia is part of the lifestyle.” It must be hard to double as an artist and a criminal.

Van Gogh didn’t have to run from the cops. Picasso didn’t have to paint his masterpieces in dark alleys. Michelangelo didn’t have to worry about dropping the soap.

But the sketchiness, the fear, the anonymity — they’re all necessary evils, SMiLE believes, because becoming a pawn in the phony, commodified art scene is a fate worse than a jail sentence.


Before I met SMiLE, I knew him only by his paintings, scattered in unexpected spaces along my neighborhood running trail. Kittens on electrical boxes. Foxes on trash bins. Van Gogh-inspired masterpieces hidden behind overgrown greenery.

I later learned that these wholesome paintings were created by a criminal, an anonymous stencil artist who illegally plasters his paintings all over the city of Boulder.

When I was offered the opportunity to join him on a covert spray painting operation, I eagerly agreed. I envisioned us working under the cover of darkness, wearing all black and traveling exclusively on the undersides of moving cars. But first, we would meet in the light of day, over coffee.

Before he would show his face, SMiLE demanded a promise I wouldn’t expose his identity. Things could go terribly wrong if his name were revealed, he warned. As we sat across from one another in a cafe, he kept his voice hushed, often mumbled.

photo - street art - smile - boulder co

[photos Lindsey Kline]

If you tell anyone about my identity, it could reach a cop,” SMiLE says. “Then, the cop’s got me on their radar. They could catch me and say, we have 42 complaints against you. Could put me in jail for a year or two.”

SMiLE got stern when I didn’t take his anxiety seriously. When I carried on our conversation at a normal volume, he told me to keep my voice down. When strangers on the opposite end of the cafe glanced in our direction, he’d insist they were “onto us.”

Strangely, it’s not the heavy hand of the law he’s most afraid of. He’s most afraid of becoming an artist with a face.


It’s the path to success that most artists take: the curators, the galleries, the brand built on their identity.

Curators are powerful players behind the scenes of the art world. They find undiscovered artists and breed them into superstars. They validate artists’ work, deeming it worthy of gallery walls and expensive price tags. They can make or break artists’ careers.

SMiLE once had curators. He hated them.

photo - smile street art - fox - graffiti

[photo Samantha Keller]

I didn’t like the way they commercialized me and turned me into a commodity,” he says.

So he joined the rebellion against the tightly-controlled art regime: the street artists. They display their work on filthy city streets, rather than posh galleries. They let laypeople judge their work, rather than professional curators. They hide in the shadows, rather than basking in the spotlights.

SMiLE claims the movement is akin to “buying locally and organically.”


Undeniably, SMiLE’s audience adores him. Even those who are supposed to oppose him — like city government officials and graffiti removal crews — admit that SMiLE’s kind of vandalism is special.

The Downtown Boulder Partnership is responsible for cleaning up graffiti around Pearl Street Mall, but often makes an exception for SMiLE, and turns a blind eye to his illicit artworks.

The City of Boulder, which has removed many of SMiLE’s works throughout the city, is now considering adding more. A potential program to reduce graffiti would partner up with SMiLE, using commissioned art pieces to cover city-owned utilities boxes.


#pink #punk #cheetah #attitudeproblem #sowhat #badass #meagainsttheworld #9th and #pearl #catchmeifyoucan #catsofinstagram #cats_of_instagram #catagram #happy #caturday #boulder #pinkpanther #streetart #stencil #grafitti #beautiful #yoga #lady #bonus

A post shared by Smile (@smileboulder) on

I talked with nearly a dozen city bureaucrats, whose careers revolve around doing things by-the-book, that confessed they were willing to break the rules to preserve SMiLE’s street art. Naturally, none of them wished to be named.

However, SMiLE is not beloved by everyone. Ironically, he’s made friends of city government, and foes of fellow street artists.

Street artists are not always the anti-establishment nonconformists they seem. Many of them have ulterior motives, SMiLE confesses. They’re attention-seekers and sell-outs.

Street artists actually have a reputation for being tools,” SMiLE says. “A lot of them start out anonymous, and a few years later they’re making a ton of money and their faces are on magazine covers. They're just waiting for their big break, using street art to project themselves into the gallery scene.”

Naturally, the hypocrisy of the street artist movement has inspired some enemies.


One late summer night, a rogue graffiti artist ran down Pearl Street, sabotaging every SMiLE painting he could find. Across every colorful picture, he used a black can of spray paint to tag his own name in hideous illegible handwriting. He single-handedly destroyed at least 15 paintings.

photo - smile street art - boulder co - dog - graffiti

[photo Samantha Keller]

This was just one assault in an endless war among street artists, taggers and graffiti artists.

In the beginning, SMiLE’s opponents had always been predictable. Old fuddy-duddys that call the cops. Graffiti cleanup crews who cover up his hard work. But now, he’s made enemies of his fellow delinquents.

SMiLE’s rivals share a common M.O. They go on a vandalism spree, deface his masterpieces with unsightly scribbles, then mock him in Instagram DMs.

They’re younger kids, and they think they’re artists because they go around at night tagging,” he says. Despite the similarities in their rituals — spray painting the city and running from the cops — SMiLE doesn’t consider taggers real artists.

If they put care and time into something, even if it’s something that I don’t really like, I respect it. If it’s something they do illegally, I respect it even more. But things like tags don’t take any courage,” he says. “I tell the taggers we’re on the same side. We’re both adding something to the city in a way that’s unauthorized and a lot of people are enjoying it. We don’t need to attack each other.”

But SMiLE’s pleas for peace go unanswered.


The last time I saw SMiLE was in that dark alleyway, acting as a lookout while he sprayed layer after layer of paint onto immaculately sliced stencils.

He chose this night to paint a picture of Jerry Garcia, the lead singer of the Grateful Dead. “I don’t even like the Grateful Dead,” he whispers to me while he waits for one layer to dry.

This isn’t the first time he’s painted something he’s not fond of. He points out his works, paintings of author Jack Kerouac, and quickly admits he doesn’t recommend any of his books. He paints cats — lots and lots of cats — because they’re less likely to get covered up by crotchety old folks and city cleanup crews.

A lot of what I paint is to cooperate with community,” he sighs. “People like cats. They leave them alone.”

Controversial pieces are simply a sacrifice he has to make as a street artist. And that’s not the only thing he’s had to give up.

SMiLE can talk for hours about the sacrifices he’s made to pursue street art — career opportunities, time, money, relationships.

To hear him tell it, he lost a girlfriend because she was worried about him ending up in jail. He gave up the chance to paint his first mural in Paris because they required his real name. He wasted time creating paintings around the city, knowing the majority of his works would be covered up. He abandoned the promise of traditional art success, and the financial stability that comes with it, to end up here — in a poorly-ventilated alley, telling his story to a reporter who’s mildly high on spray paint fumes and doesn’t know the first thing about fine art.

Ultimately, I don’t think SMiLE minds that I’m dumbfounded about the art world. In fact, I think he prefers it that way.

SMiLE made his sacrifices to pursue art that’s accessible to the masses. Art that’s not just for snobs strolling down the terrace with their immaculately-groomed poodles, shopping for paintings that would look divine in the parlor. Art for the local joggers. The drunk frat boys. The smelly hobos.

So take notice next time you spot SMiLE’s masterpieces on dirty dumpsters, old fences and dank alley walls. That art is for you.


I learned while living in Paris that I'd rather eat a five-bite meal with friends and still be hungry afterwards then eat a five-course meal by myself and be full and lonely afterwards. #sharing is addicting, the first step is the hardest step. This #painting of a #rasta is nailed to a dead and charred tree somewhere along the Anemone Trail above #redrocks in #boulder . Whoever finds to it first gets to keep it. #finderskeepers #share #streetart #dountoothers #goldenrule

A post shared by Smile (@smileboulder) on


#impressionist #kitten #looking for #love #validation #outside #self #whatabummer #neverending #quest #reincarnate #seek #holygrail #somewherearoundtheworld #almostgotit #nexttime #forsure #cat #streetart #stencil #cats #paris #impressionism #iftheshoefits #cats_of_instagram #catsoninstagram #catsofinstagram #caturday

A post shared by Smile (@smileboulder) on


#postmodern #stencil #impressionism in #nature on #foundobjects #2pac #smile #big #lifeisbeautiful and #painful #allatonce #thuglife #westcoast #rider #alleyezonme #boulder #streetart #spraypaint #pochoir #art #stencilart #stencilism #yolo #midnight #ninja

A post shared by Smile (@smileboulder) on


[cover photo SMiLEfineart via Etsy]