A Legendary Street Artist Made A Love Letter To Detroit By Taking Over 50+ Billboards Around The City

Detroit billboard street art by Kai

via Kai, with permission

Every city sees its share of ups and downs. Detroit, however, knows how to embrace this rollercoaster of highs and lows deep into its urban soul.

The Motor City has always stayed true to its cultural heritage, from Motown to the Fox Theater to coneys and Detroit deep dish pizza. The first time I felt Detroit’s distinct vibe was when I was in town for the annual North American International Auto Show during the artic chill of winter. One night, I bundled up and headed down street from the Rennisance Center to Sweetwater Tavern for dinner for a local buddy, at his recommendation. It was the exact opposite of the frozen tundra outside: a lively place to kick back and hang after a long day on our feet.

The chicken wings were some of the best chicken wings I’ve ever had in my life. I enjoyed myself so much that night, I had a moment of clarity just how special this city is to the United States.

Pop culture often celebrates Detroit for its sound, the Hitsville USA melodies of the White Stripes, Smokey Robinson, Stevie Wonder, Eminem, and so on. But there’s also a visual Detroit love story that’s not narrated through song or words, but with the visual arts that deserves just as much recognition.

What better place to tell that story than a billboard? It’s the ultimate medium of commerce and expression – an ethos Detroit knows very well.

Detroit, after all, has an aesthetic.

Kai, the renowned street artist from Los Angeles who studied at California Institute of The Arts and L’Ecole des Beaux Arts in Paris, felt that creative vortex of energy many experience when they take a trip to Detroit for the first time. “I really fell in love with the idea of these old cities being revived,” Kai tells me. This wasn’t just about the physical structures, but the soul of the city—its people, its stories, and its undying spirit. “These cities have lived, and the younger folks who’ve stayed are weaving new tales of revival. They understand and appreciate the essence of the place,” he added.

Kai is a visual artist, first and foremost, but through his work he’s also one heck of a storyteller. The Kai’s work comes alive with “IF,” short for “Imaginary Friend.” Think of “IF” as a cartoon with an edge—a mix of humor and heart, painted in broad strokes and fine lines.

His depictions of “IF” sell for thousands of dollars in fine art galleries around the world.

“IF” isn’t just doodles and sketches. It’s is defined by its universalness – it’s genderless and has no race, a symbol for the raw human experience we all feel.  This character captures the now, reacting to today’s buzz while echoing timeless vibes of love, hope, and those oh-so-familiar life hiccups. And those raw emotions? They’re out there, unfiltered, making you stop, think, and maybe smirk or sigh.

Detroit billboard street art by Kai

via Kai, with permission

See an “IF” on a side street or perched in a gallery in New York or Miami, you’re instantly in a tête-à-tête with Kai’s universe—a fresh, quirky take on life, with a sprinkle of human reflection.

Kai’s first trip to Detroit was an invite from a collector.

“I really fell in love with the idea of these old cities being revived and given a new life of renaissance by the younger people that have lived there their whole lives and understand and appreciate the city,” Kai says. It’s a sentiment that resonates with anyone familiar with the spirit of Detroit—a city proud of its history, eager for its future.

Kai asked if he could return to do a little street art after falling in love with the city.

Instead, he got connected with another collector who works in advertising.

There was an idea: What if he took over some billboards, completely authorized?

The project was audacious: Kai took over 50+ billboards across the city, overlooking many-a bustling highway and street corner.

“What we did was kind of interesting because I still have a vandal street art feeling of going up there and taking over a billboard,” he explains. “But I’m doing it with the respect and authorization of someone in the city. And I’m not defacing and harming the city in any way. So it’s just a beautiful love letter to the city of Detroit and the grit and the renaissance it’s having. I really love the project. It’s one of my best projects yet.”

Detroit billboard street art by Kai

via Kai, with permission

Many artists inspired by Detroit focused on its industrial, blue-collar past. But Kai chose another path. “It’s not about Detroit’s history, as magnificent as it is,” he reflected. “It’s the pride, the unparalleled passion of its people. That’s something else.”

“People here wear their love for the city on their sleeves. It’s this pride and passion that moved me, drove me,” Kai says. His art, thus, aimed to mirror this sentiment, presenting it back to the people in colorful, abstract forms.

Detroit billboard street art by Kai

via Kai, with permission

A Love-Letter To Detroit

Each of Kai’s creations on these billboards tells a different story. “I didn’t want repetition. Every piece is an experience, an emotion in its own right,” he elaborated. From intricate patterns that mirror the intricate lives of Detroiters to bold statements on love, life, and belonging, Kai covered a spectrum of emotions.

However, the heart of his work was the community. “Detroit’s community vibe is something I haven’t experienced elsewhere,” he revealed.

Kai was especially moved by local initiatives, like the temporary Cider Mill, showcasing the residents’ love for traditions and community bonding.

“Like, I went to a cider mill,” Kai says. “I had never been to a cider mill in my entire life. It was amazing. They’re like, oh yeah, it’s only here for three months. I’m like, ‘three months? All of this is just for three months?’ The line was super long and everyone was coming out to support it on a Tuesday afternoon in the middle of the day. And I was like, is it always like this? They’re like, yeah, of course. The cider mill opens, everyone shows up to support it. We all love the donuts, we all love the apple juice. We all love the apple pie. And we come here and we support our local cider mill. There’s something beautiful to say about this kind of community aspect that Detroit has that I haven’t found in other large cities.”

Detroit billboard street art by Kai

via Kai, with permission

“So I wanted to just kind of write a love letter to the city in that sense,” Kai continues. “That’s why you have like, love holds us together. Like the heart is holding the people into the city, they’re staying there. A lot of people have run away from the city. A lot of people have fled, but the heart of the city of the community is keeping them in there.”

Organic Discovery and Reception

In an era of aggressive promotions and digital blasts, Kai’s billboards were a breath of fresh air. There were no grand announcements, no media hypes. No aggressive, over-produced social media sizzle reels. People stumbled upon them, and the joy of organic discovery was authentic and real. “The feedback’s been unreal,” Kai beamed. “DMs, texts from Detroit locals—it’s heartwarming to see the love.”

He added, “Art, when discovered naturally, creates a more profound connection. It’s spontaneous. It’s real.”

Leaving Impressions

In the advertising industry, every look an ad gets is measured as an impression. Kai’s billboard art project, however, is pure narrative over numbers.

Every piece of art, much like every individual, has its own story. Kai firmly believes in the magic of letting these stories have on their own accord. “I’m gonna let it live a little, let it have its own story before I tell its story,” Kai reflects. “In life, things have their story… It’s best when other people tell the story before the artist does.”

This approach allows for diverse interpretations, making each artwork a personal experience for the viewer. It fosters a bond between the artist, the work, and the observer, letting many tales coexist.

Detroit billboard street art by Kai

via Kai, with permission

Embracing the vibrancy of urban living

Art that’s so approachable in everyday life is the kind of spontaneous thing that makes urban life so damn special.

In a world where cities often lose their identities with glass structures, cookie-cutter architecture, and indistinguishable skylines, Kai’s Detroit billboard residency reminds us of the importance of a city’s past and how it marinates into a community’s vibrancy.

It’s a reminder to city folk to look up from your phone and keep your head on a swivel. Just like those billboard impressions, great street art is a fleeting whisper into the subconscious that leaves an echo, tickling the brain of the passer-by that takes notice.

And the cherry on top? In a world plastered with ads on those billboards, his art doesn’t have an agenda—it’s not selling; it’s storytelling.

Detroit billboard street art by Kai

via Kai, with permission

Brandon Wenerd avatar
BroBible's publisher and a founding partner, circa 2009. Brandon is based in Los Angeles, where he oversees BroBible's partnership team and other business development activities. He still loves to write and create content, including subjects related to internet culture, food, live music, Phish, the Grateful Dead, Philly sports, and adventures of all kinds. Email: brandon@brobible.com