Paul Richmond paints so people feel seen

Paul Richmond says what he makes in one sentence: "Paintings and artwork that make people feel seen. Ideally, with a little color, a little humor, and occasionally a man in his underwear."

He paints from a studio in Monterey, California, walls stacked with portraits of men. He turns men into pin-ups for his Cheesecake Boys colouring books, paints strangers live on Instagram with both of them in their underwear, and runs art projects for young people who have been bullied. He once delivered a painting to Dolly Parton and hung it in her living room himself.

He answered our questions by email. Here he is in his own words.

A three-year-old with a pencil

What was he drawing back then? "Disney princesses, characters from my favorite stories and cartoons, and pretty much anything that caught my eye or fired up my imagination," Paul says.

"I started taking painting lessons with Linda Regula just before my fourth birthday, and she was wonderful at teaching me the fundamentals while still letting me choose what I wanted to paint. That balance was invaluable."

“I learned the technical skills, but I also learned that art should be driven by curiosity and excitement.”

Turning the tables

Cheesecake Boys started with a question. "I've always loved classic pin-up art and its playful, innocent suggestiveness," Paul says. "At some point, I started wondering why women got to be celebrated as glamorous, cheeky sex symbols while men were largely left out of the fun. It seemed like a missed opportunity, so I decided to turn the tables."

"I wanted to give men the same opportunity to be beautiful, playful, and a little ridiculous without taking themselves too seriously."

The project is now three published colouring books. "Apparently, people really do want to spend their evenings coloring handsome men in their underwear. Who am I to stand in the way of that? I consider it a public service, really."

“I'm bringing joy to the world one bulging pair of briefs at a time.”

A door a lecture never would open

Humour runs through almost everything Paul makes. Why does it matter?

"Humor is a wonderful way to sneak past people's defenses," he says. "Sometimes you can communicate something meaningful to someone who might otherwise shut down if you approached the subject too seriously."

“A little laughter can open a door that a lecture never would.”

"Life is complicated enough without making everything a solemn affair. Laughter connects us, and I love finding ways to bring a little of it into my art, even when I'm exploring more challenging subjects."

What resilience looks like

Paul co-founded the You Will Rise Project with Linda Regula, the teacher who gave him his first painting lessons. "The You Will Rise Project uses art to empower young people who have been impacted by bullying," he says.

"They've taught me what resilience really looks like. It's not necessarily about being fearless or pretending that nothing hurts. Sometimes it's about finding the courage to tell your story, to make something beautiful out of a painful experience, or to discover that you're not alone in what you've been through."

"We started the project hoping to give them something valuable, but they have given us just as much in return."

A week of Queertopia

With fellow artist Briden Schueren, Paul runs Queertopia residencies on college campuses. "We both grew up struggling to find ourselves and our communities, and we want to help make that journey a little easier for queer young people today," he says. "We can't go back and give our younger selves the experiences we needed, but we can help create them for someone else."

For a week, the two paint collaborative portraits from photographs sent in by people from that community. "We paint in a public space from morning until night, inviting anyone who wanders by to hang out, talk, make art, or simply be curious. We put out art supplies so people can join in, regardless of their experience level. No art degree required!"

At the end of the week there's a pop-up exhibition of their portraits alongside work by students and locals. Everything is sold, and all the money goes to a queer charity the students choose.

“It's powerful watching people who have spent years feeling invisible suddenly realize they're part of a community.”

One hour, one painting, no pants

Brief Encounters is Paul's livestream on Instagram. He paints people from around the world while having a real conversation with them. "The premise is simple: one hour, one painting, no pants!" he says.

"Both the model and I wear our underwear, which adds a layer of vulnerability to the experience. We're putting ourselves out there in more ways than one, and I think that helps create a different kind of connection."

"We end up talking about everything from art and identity to relationships, insecurities, and the wonderfully weird business of being human." People watching can join in through the chat, ask questions, and draw or paint along.

"It's part art demonstration, part intimate conversation, and part social experiment involving questionable wardrobe choices."

Dolly

Paul has painted commissions for big names, but one surprised him most. "Dolly Parton was definitely the biggest surprise, because she was my childhood hero," he says.

"I grew up in a small Midwestern town in the 1980s, when I didn't have much access to queer culture or representation. I didn't even know there were other people like me out there. But there was something about Dolly that spoke to me."

"She represented the possibility that there might be a place in the world for someone who didn't quite fit the mold."

So when Dolly commissioned a painting of butterflies for her living room, he was floored. "I actually got to deliver the painting and hang it in her house. There's something surreal about having a childhood dream come true in such a literal way."

“The little kid who was drawing princesses at the kitchen table would have absolutely lost his mind.”

Barcelona next

Paul is painting a new series for a show at BNude Gallery in Barcelona in October 2027. "It's always exciting to begin a new series because you have a destination in mind, but the paintings have a way of surprising you along the way," he says.

He's also keeping Queertopia, Brief Encounters and large-scale murals going. "Sitting quietly alone in a studio and painting isn't quite enough for me. I also need to invite people into the process, take my pants off for the internet, and keep dreaming up new adventures every day."

Find your people

We asked what he'd tell a young queer artist starting out.

"Don't sacrifice who you are or how you see the world to fit someone else's expectations," Paul says. "Your perspective is valuable precisely because it's yours, and the things that make you different may ultimately be the things that make your work meaningful to someone else."

"You can't control how everyone will respond to your work, and you shouldn't try to. But there are people out there who need to see what you're making."

"Keep making things that excite you, keep learning, and find your people. They may not all be in your hometown, or even your country, but they're out there. And please remember that you don't have to wait for someone else to give you permission to call yourself an artist. You can start right now."

“We need more people brave enough to show us who they actually are.”

Paul goes live with Brief Encounters every other Tuesday at 11am Pacific time. Follow him on Instagram at @paulyworld.