For local artist and Detroit School of Arts alum Phillip Simpson, a smile is not just a smile – it's a brand, an art, and a way of living. He credits the educators at Detroit Public Schools for giving him the tools and encouragement he needed to build his artistic career.

Simpson was jovial as he strolled into his art studio on a bright late summer day, the signature smile on his sweatshirt matching the grin on his face. Brightly colored paintings – most of whom incorporate Simpson’s stylized smiley face – lined the walls.  

Simpson’s work is also writ large and small across the city, from small building murals and art gallery collections to a giant smiley face mural on the side of the Broderick Tower in downtown Detroit, which stood for nearly two years before it was damaged by storms in summer 2023. 

His paintings, art, and clothing line – a brand known as The Smile Brand – is a mission to spread positivity and kindness.  

“I pray that my artwork inspires a feeling of joy,” he said.  

How Educators Made a Difference in Simpson’s Life 

For as long as he could remember, Simpson created art, starting with cartoon drawings of The Lion King, Pocahontas, and Teenage Mutant Ninja Turtles as a child. But it was his mentors – both inside and outside of Detroit Public Schools – that gave him the tools and encouragement he needed for a successful career as an artist and entrepreneur.  

His love for art was first nurtured in a Saturday art program around the time he was in middle school. Simpson said the structure of a planned weekend activity kept him from getting involved in trouble in the streets of Detroit. He learned about the ins and outs of creating art, including technical techniques like oils, charcoals, and more; as well as the business of framing and shipping art.  

He also met Joyce Ivory, one of his first mentors, who made him feel seen and valued. That Saturday class and his education at Marcus Garvey Academy built the foundation for him to enter the Detroit School of Arts (DSA) in 1996, where he had the opportunity to practice his craft every day.  

“You had three art classes a day, so that means every day I’m taking drawing and painting. Every day you’ve got a class about what you do. For me, and a few other kids I know, art is all I ever wanted to do, so drawing every day was incredible,” Simpson said.  

He also had amazing teachers who nurtured his passion for art. Gayle Glenn and Henry Boyd stood out as some of his favorites. They instilled knowledge of art history and techniques and also encouraged him in his craft.  

All good educators had a few things in common. Simpson said the best teachers gave constructive criticism to improve his work and made him feel seen, valued, and heard. They went the extra mile to show that they cared, such as purchasing extra art supplies for him to take home, staying after school or during their lunch break for tutoring, or calling his parents to discuss his academic and social-emotional progress.  

“Whatever it took, they were there. There were middle school teachers that weren’t art teachers that played a huge role in my upbringing. So, every teacher wasn’t an art teacher that made a difference in my life, but I think overall, I had a really good group of educators that made me who I am. I don’t underestimate a teacher’s impact at all.” 

DSA also fostered a nurturing environment where everyone was valued and cared for. Simpson said the school’s then-principal and founder Dr. Denise Davis-Cotton knew everyone’s name when she walked down the hallway.  

Smiling Through Adversity  

But the road to Simpson’s current success was not always easy. He said he hit a low point in 2011 when his first clothing store closed, resulting in the loss of income and a social support network. It was a business that he thought would be around a long time, so the closing only two years after the store’s opening came as a major blow.  

To cheer himself up, he started painting smiles. He never stopped, and the Smile Brand was born. Simpson began getting publicity with his building murals around the city and the launch of his clothing line in 2012.  

He learned several tips for young entrepreneurs and artists along the way. Simpson said finding a mentor, especially when you’re young, will help you succeed, as well as surrounding yourself with positive, like-minded people who encourage you and strive for success themselves. He said he’s learned to save and invest money so that he can plan for unavoidable slow periods in the business. He also emphasized the importance of young artists spending time to practice their craft.  

Giving Back 

He gives back to Detroit youth through various programming and projects at schools both inside and outside DPSCD. Most recently, he completed a mural in the library of Charles Wright Academy. The school received the library makeover as a prize for being one of the top performers in last school year’s District-wide reading challenge. He hopes to continue to give back by providing programming on entrepreneurship and art in Detroit schools.  

“From my childhood, we had so many cool visitors in school. I was thinking, ‘This person is dope, and they’re coming back to talk to us?’ Sometimes that extra person may bring something the teachers don’t have the expertise in,” Simpson said. “Teachers or administrators bring me in because I’m the example of, not only am I from the same neighborhood most of the time, I’ve figured out a way to follow my dreams and it’s pretty cool to tell kids, ‘It’s possible’.” 

Simpson also balances his career and volunteering with his family, comprised of his wife, Syretta Simpson, six-year-old daughter, Journee, 22-year-old daughter, Jadori, and dog, Rocky.  

Not only is his family his biggest supporters, but they’ve also served as sources of inspiration. The lessons he teaches Journee – including the importance of being true to yourself – are featured in several of his paintings.

Interested in attending Detroit School of Arts? 

Detroit School of Arts application window is open! Visit detroitk12.org/dsapathways to learn more.

Where You Can Find Phillip Simpson’s Work  

To see more of Phillip Simpson’s work, follow him on Instagram @artbyphillipsimpson or on Facebook @Art by Phillip Simpson. You can also visit his website The Smile Brand for occasional merchandise drops.