It’s Creepy and it’s Kooky, Mysterious and Spooky — The Whimsical World of Artist Kyle Smile
Updated: Oct 20
IT'S ALWAYS HALLOWEEN in the whimsical world of Kyle Smile, a multimedia artist whose happy and haunting work can be found lurking in corners and corridors across West Palm Beach and beyond.
At the popular downtown nightclub Respectable Street, a panorama of mischief-making creatures wreak havoc across the walls of the back patio, a constantly-changing action cartoon the artist’s admirers call his masterpiece.
On the south end of town, two dogs serve burgers and fries to four cats at a lunch counter in a happy outdoor mural that greets customers arriving from the parking lot at the diner Howley’s.
For a time, a Godzilla-like monster roamed strolled among skyscrapers across the side of a house in a residential neighborhood near downtown Lake Worth Beach, one of the artist’s earliest works. Variations of it have appeared on the cover of PureHoney magazine.
His latest works are meant to be picked up and cuddled — adorable plush animals turned inside out and decorated with bloody scars.
“I like to call it a little creepy, a little cute, a little demented, or somewhere in between those worlds,’’ said Kyle Hess, the popular underground artist better known by his nom de plum Kyle Smile. (Since just about everyone, even his family, know him as Kyle Smile these days, that’s the name we'll use for this story.)
He has other creative outlets, too. He writes music, makes pop up art and creates sculptures out of junk electronic parts. Once in a while he dabbles in film.
In 2011, he won an award at a Lake Worth film festival for a stop-motion animation called Seeds, which starred some orange seeds and pieces of fruit. He performed the film’s music score.
From time to time, he plays piano for the lunch crowd at Hullabaloo on Clematis Street. A few years ago, he played an accordion at the Lake Worth Street Painting Festival.
But his go-to outlet is painting, no matter what the canvas, be it paper, concrete or coconuts.
His work has been displayed over the years at places like Howley’s, Harold’s Coffee Lounge in West Palm Beach and Coaster’s bar. But outside of social media, he has never been one to aggressively market and promote his work.
Still, his art is in demand, and not just among underground arts-scene insiders.
“He has so much diversity in what he does,’’ said Alan Sennett, a longtime Respectable Street emcee and promoter who is among Smile’s earliest admirers.
“He has his own style but he also has like 20 other styles. It’s hard to put in words. How do you explain Jackson Pollock’s art? You can’t. You just have to see it.’’
Perhaps the best way to experience it is to visit the back patio at Respectable Street, a popular outdoor alcove with a bar and stage.
Wrapping around the cozy hangout spot, a whimsical panorama of aliens and creatures plays out across four walls, a work in progress since Hess first started painting it in 2014.
The mural has a life of its own, nurtured by subtle and mischievous changes Smile makes every few weeks or so to cartoon creatures who induce patrons into interacting with them.
One Saturday night, the eyes of a monster might be looking to the left, a week later to the right. Dialogue clouds above the character contain quotes that change every few weeks.
“It’s like an eight year long performance art piece on a wall,’’ Sennett said. “It’s something that has to be experienced over a long period of time. All the regulars have been watching it evolve. They're kind of part of it, too.’’
And that’s the point.
“My idea was to mess with the regulars,’’ Smile said, explaining why the same crow that was seen sitting on a creature’s shoulder last week can be seen pecking its eyeballs out today.
During the pandemic shutdown, he painted masks on a few of the creatures, a subtle surprise months later for returning Respectables regulars.
“Some nights I’ll be having a beer back here,’’ he said, “and people will look at the mural and look at me and go, ‘That’s different, right?’ I’m like, ‘I don’t know. Maybe.’’’
Like the creatures he creates, Kyle Smile’s artistic spirit almost always comes out at night, a door that opened one day 28 years ago.
He was about 8 years old, on vacation with his family, when walked into a room where his parents and older brother and sister were watching A Nightmare on Elm Street. “All I saw was Freddy’s clawed hand and I ran out of the room.’’
Scary movies haunted him for most of his childhood.
“His older brother would trick him into going to one of these movies and he would be petrified,’’ recalled their father, Dan Hess.
A turning point came when he worked up the courage to see the movie Edward Scissorshand.
“I thought it was going to freak me out, and then I watched it finally, and it’s a comedy! It's like the most precious movie. There's nothing scary about it,” Smile said.
“Hindsight, that's kind of like my art.’’
Like all art, Kyle Smile creations are ripe for interpretation. He mentioned a painting he made of a horrific monster holding a child’s hand.
“Has the demon kidnapped the kid or are they best friends?’’ he said.
Dawn Hess, Kyle’s mother, said she’s amazed at how her son channeled those early traumatic movie memories into such fun and whimsical art.
“It's almost like when you conquer your fears,’’ she said. “He got over that, and now he has put a cuteness to those images.’’
The “cuteness” is inspired by the qualities she admires most about her son.
“He has the sweetest, kindest soul of anyone. He is the most loving person,’’ said Dawn Hess, a massage therapist.
Art was an early part of his life.
Like most kids, he enjoyed drawing as a kindergartener. He remembers positive reactions from classmates to a realistic sketch of a shark he drew in second grade.
“My dad was a lifeguard so I knew what sharks looked like,’’ he said.
As he created art in between classes over the years, he continued to attract crowds of students.
He found another outlet in his teens playing music. By 17, his creative passions led back to painting and drawing.
“That’s when I went from someone who likes to draw to someone who wanted to be an artist, someone who had something to say,’’ he said. “I forced myself to be a better artist.’’
By 2013, PureHoney magazine founder Steve Rullman discovered his art and helped arrange the logistics for the Godzilla mural Smile painted on the side of a house in Lake Worth Beach.
Rullman also connected Smile with Rodney Mayo, owner of Respectable Street, Howley’s and other popular South Florida eateries and hang-out spots.
Mayo invited him to join his stable of artists who use the walls of his establishments as their canvases.
Smile created murals at Vagabond’s in Miami and Howley’s, but the walls of Respectable Street, especially the outdoor alcove in the rear, have called to him from the beginning.
“He kind of adopted us,’’ Mayo said. “We started seeing some of his work on the patio before I ever met him. Of course, I loved it and he asked if he could just add to it when he had time.’’
Seven years later, he’s still adding to it.
“Sometimes I won’t notice something and then when I do I wonder if it's been there for years or he just did it last night,’’ Mayo said.
Mayo, who is known for replacing the artwork at his clubs every few years, said he has no plans to touch Hess’ Respectables panorama.
“It has become part of the patio at Respects. We will let him to continue with whatever he wants to do out there for as long as he would like.’’
Smile and his girlfriend, artist Kacee Weber, share a cozy pool house behind a Lake Worth Beach home.
When they’re not out hiking or camping in Florida’s wilderness areas, they’ll work on their art together at home or showcase their work (Weber paints and creates dolls) at festivals and events around town.
These days, you might run into them at night at the South Florida Fairground. Smile and Weber are among the costumed actors putting the fright into Fright Nights, the Halloween spectacle of haunted houses and amusement park rides.
But in many ways, the back patio at Respectables is the Kyle Smile studio, a place where he exorcises demons that sometimes haunt him with anxiety, insomnia and depression.
“If I don't have an outlet, I go crazy,’’ he said as he touched up his mural one day in October. “Most of this stuff you see was done without sleeping.’’
He works the night shift at the Posh Pet Hotel, then often goes straight to Respectables in the morning to paint until early afternoon.
“Respectables is a pretty precious place to me,’’ said Smile, who remembers sneaking into the place as a teenager to see his favorite band, Pygmy.
Even the name of the club is perfect, he said, “because the people who come here are just really good people. That’s why I’m so respectful of this place. I'm so happy to be able to do this.’’
Mayo also allows Smile to set up a table on the patio to sell his plush “inside outs,’’ as the artist calls the stuffed animals he acquires at Goodwill, World Thrift and through donations from friends.
After undoing the thread and turning them inside out, he studies their new likenesses for inspiration.
“If there are weird things that didn't exist before but are there now from being turned inside out, I work with whatever that is,’’ he said. “If there’s space for four eyes instead of two, you put four eyes in there.’’
One of his first inside outs was purchased by Sennett, who took the odd-looking bear on a cruise to Alaska where he and his wife posed the plush toy for photos on the deck of the ship as they cruised by glaciers and mountains.
Several Kyle Smile pieces decorate the walls and shelves of Sennett's Palm Beach Gardens home.
“We’re not art buyers, but his little creatures just speak to us,’’ Sennett said.
The inside-outs — they’re something of a paradox for Smile because he is an animal lover, especially cats — can be purchased for as little as $25 at www.Kylesmile.com and his instagram account, _kylesmile_.
They’ve been in high demand lately and he has bruises on his thumbs (from working the needle) to prove it.
When he puts the inside-outs away for a while to let his thumbs heal, he returns to his happy place on the walls on the back patio at Respectables.
As he was adding dayglo paint to a row of aliens the other night, he talked about his plans for a section of bare wall on the left side of the patio bar.
“That wall over there will get something new,’’ Smile said. “I’ll look through my art and find something that sticks out so people will walk back here and go, ‘That’s new!’’’
“And since it's October, I want it to be creepy.’’
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