The Joy Factor

Another visit to the modern mystic and painter, Milo Redwood

Posted 5/11/22

Meeting the local lyrical expressionist, Milo Redwood, is an experience that feels serendipitous and even synchronistic somehow. Skeptics will try to deny or explain away the palpable energy shift …

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The Joy Factor

Another visit to the modern mystic and painter, Milo Redwood


Meeting the local lyrical expressionist, Milo Redwood, is an experience that feels serendipitous and even synchronistic somehow. Skeptics will try to deny or explain away the palpable energy shift one feels walking through the little blue door of the Hastings Building, through which they enter a new world entirely, smelling of wood, wine, paint, and incense.

Redwood himself is a gentle force (nicknamed “the Fifth Mystic”), settled into his plush, chartreuse chair, hands folded over belly, with an intoxicating smile and even more exhilarating laugh. He found Port Townsend more than 25 years ago, has 25 acres outside of town and most importantly, his tiny alternate universe downtown.

The studio feels like art as well. The floor is be-speckled and the walls and ceilings are enrobed in primary color visions. Previously enjoyed bottles of red wine sit in a collection beneath the record player in the corner. The lights are warm and the unmatching seats are in a circle.

But, when the curtain is drawn in the window of the Water Street studio, Redwood is working. Callers ought to return at a later date.

In fact, Redwood only works privately. No one has ever seen him paint in all his years. To him, it’s a vulnerable and entirely encompassing experience that he prefers to keep for himself. His art manager, B. Barclay, pokes fun at Redwood, revealing that, actually, someone has seen him paint. Rather, some crew and millions of viewers have seen the mythical process. GoDaddy, the website creation platform, was in town scouting for locations.

“He was in here, still creating in the pandemic, so he’s got the door open, he’s painting and GoDaddy walks in with cameras and they’re like, ‘Can we film you?’” Barclay explains, giddily grinning. “So he sends me a link from GoDaddy, I’m like, ‘So this is the first time I see you paint, is a GoDaddy ad?’”

Of course, it was a show. Redwood was pretending. He would never truly pull back the curtain, not even for Barclay.

Seeing Redwood’s paintings makes it understandable that he creates alone. They’re raw and vulnerable, like the page of a diary (if the diary were made in brilliantly bold colors with expert composition). Some include words or abstract versions of recognizable shapes but most are like an acrylic printing of Redwood’s brainwaves — beautiful and unpredictable.

He describes the process like a trance. He’s partly joking but it’s true that he paints by pure feeling.

“I wouldn’t call it a chant but I’m in the zone,” he said.

He paints  by music, and typically, beer.

On a wall in his studio, he wrote the formula in big, grocery list letters: “Beer, Monk, Paint.”

He has a moment of sort of communion, he said, when he cracks open the beer, and puts on his music of choice, jazz pianist Thelonious Monk, as it was five years ago when he wrote down the recipe, and paints.

Some of his paintings, when flipped over, reveal the music behind it and the time Redwood made it. Fingering through a box of earlier, smaller works, the backs contain notes like, “The Dead 1 p.m.”; “Silence”; “Almost noon, acoustic mix.”

He said his paintings are pure feeling and when he’s in the zone, he’s really in it. Barclay said they’re journal entries.

“It probably sounds trite but they are visual journal entries, like I’m not confused by that,” Redwood explained.

Then, in a jokingly wistful tone, said, “They came to me in a dream,” and laughed at himself.

His creativity bloomed in the Midwest metropolitans he hopped through as a child, moving here and there with his parents. He remembered the beauty of Oregon in the beginning of his life and is almost grateful he didn’t stay long.

“The salty air and bluebirds and all that, it was really a mythological start. I don’t know if I’d even paint if I stayed in so much gorgeousness,” he said.

Redwood credits the graffiti surrounding him in those Midwest cities as an influence in his work now. Barclay calls his style urban street art mixed with Picasso.

Now that Redwood has done his traveling, including adventures like cross country trips on motorcycles, and is back in the spurring radiance that is the Pacific Northwest, he’s not going anywhere. In fact, he hasn’t left the Olympic Peninsula in over seven years. With one exception: “I think I took someone to the airport.”

“Big mistake. Don’t ever volunteer for that. It took me like two days to get over that I’d been off the Peninsula. It’s terrible!” he laughed.

But the truth is, regardless of where he lived or didn’t, Redwood would be a painter; he knows this. He said there were several early indications that he was put on Earth to paint but the sharpest moment came when he poured a new tube of paint onto his palate. It was an oil paint from Germany he had never tried before, in cobalt blue. It made him cry.

“Figures,” he said.

He doesn’t cry easily, which made the moment all the more powerful.

Barclay said that sums up what Redwood’s art means and explains why he is so connective: “Someone who has that connection to beauty, where they can take that moment and see that blue and appreciate it. There’s so much bombarding our minds nowadays, we’re constantly thinking we have to go and a painter in Port Townsend is pouring out blue with tears in his eyes.”

Both Barclay and Redwood are more concerned with connection than anything else. That’s the joy factor.

They want to cultivate quality time with the people who are magnetized to the studio by its ineffable energy. While Redwood’s paintings have increased 1,000 percent in value, he still has trouble with the monetary side of his craft.

“It’s the value of the transaction. It’s not the cash value,” Redwood said.

He and Barclay agree that if all parties are smiling when they walk out with a painting, then it was the right price. They explained that if it’s going to someone who clearly cherishes the detail of every inch of the painting, which most people do, then they know the painting is truly for that person. “You can’t really put a price on art,” Redwood said.

Barclay said it all boils down to the motion, the smile, the flow of everything. And that’s when Redwood gets really creative. He’s often most inspired right after selling a painting, amped on the experience of providing someone joy and connecting with them, intermingling in one another’s stories.

“We just love people who love Milo’s art,” Barclay said.

“Well, I love people who don’t love my art,” Redwood corrected.

“That’s true,” Barclay considers, adding with a laugh, “Milo, you’re in love with people.”

“Yeah, that’s my cross to bear.”

When Barclay brought up how much he sees a Redwood painting being worth in the future and said, “Now what does that mean?” Redwood busted out laughing.

“Means I’m dead! Means I’m pushin’ up lilies behind some barn somewhere!”

Barclay laughed with him but said it’s not about the artist dying. It’s about how they live — that energy emanates from their work and that’s what determines the worth.

Still, Barclay pokes fun at the difference in the joy factor and the art world he’s used to in Los Angeles, the difference in pricing especially. Redwood chimed in, hypothetically quoting the business-oriented dealers of big cities, “‘Why don’t you sell Girl Scout cookies, make some real money!’”

Redwood has joined in on certain trends, though. His website and Instagram offer a virtual gallery tour, fit with augmented reality. Visitors can point a phone and put a painting on the wall in their home, move it around, even flip it around and inspect the back.

The website also offers investment opportunities. It almost feels counter-intuitive that the full-grown hippie would jump on the NFT train with his disarming, other-worldly paintings.

But that’s Redwood. There’s a new element around every corner. Barclay explained that they’re navigating the present while incubating their authenticity. “Something special that is ineffable is literally happening in Port Townsend, in this room, that’s affecting the global art community every day but at the same time we just stay doing what we do and it’s beautiful…. And we also started a TikTok.”

“HE started it!” Redwood shouted. They both dissolved into laughter.

Find Redwood’s work and more about the artist at and on Instagram @MiloRedwoodArt.