Painting the Misfits with Jaime Diffee

By Dakota Parks for Inweekly

If you’ve ever spotted an odd little critter staring back at you from a mural in Pensacola, chances are you’ve already encountered Jaime Diffee’s work. From thumbs-up possums and armadillos in combat boots to cowboy-hat-wearing toads, Diffee’s work always seems to create its own strange little world.

“I’m enamored with all critters, varmints and beasties,” Diffee said. “I especially love animals, like possums, that are generally regarded as pests or just ‘gross’ but actually do so much background work in helping their native ecosystem. There’s something very relatable to that while growing up queer in this society. Outcast-to-outcast, I see the joy and importance in these little guys.”

As the May Artist-in-Residence at 309 Punk Project, Diffee is spending the month bringing overlooked creatures into the spotlight and inviting the community to do the same.

By day, Diffee works behind the scenes at the Pensacola Museum of Art as preparator and curatorial coordinator, installing exhibitions, caring for the collection and helping shape how art shows up for the public. Being around so many different approaches to art has quietly inspired their own practice.

“With my role, I often get to experience hands-on a diverse range of mediums and artistic practices from artists nationally and internationally that I wouldn’t get to see otherwise,” they said. “I’m constantly absorbing little aspects from all these different ways art is approached, which only makes me love the simple act of creating more.”

Trained in traditional oil painting, Diffee’s work is rooted in careful observation but has gradually loosened into a more playful, expressive style. While their background leaned toward realism, practical constraints like limited studio space have pushed them toward acrylics—a shift that’s opened up new possibilities and allowed their work to become more experimental and a little weirder.

“The nature of acrylics forces me to be simpler and more direct with my line-making and color usage,” they said. “That allowed me to step away from realism and just paint little guys.”

Those “little guys” have become something of a signature. Whether it’s a tattooed armadillo or a possum family in a swamp, Diffee’s creatures carry an unmistakable personality, bringing human and animal imagery into close, sometimes uneasy proximity. It’s a visual language that fully clicked into place during the CUBED 2021 mural festival, where they felt a newfound freedom to embrace their creature niche.

“My doodles have always been a bit more cartoon-y and expressive, but it wasn’t until the CUBED 2021 mural fest where I felt free enough to just be open and weird about the creatures I paint,” Diffee explained. “You don’t need to paint a masterpiece every time; sometimes you can just paint a possum giving you a thumbs-up.”

Diffee is a regular muralist for the Pensacola Museum of Art’s annual CUBED installations, creating vibrant pieces on the 8-by-8-foot cubes located in Museum Plaza. Their latest mural, completed just a few weeks ago, features a winking royal feline: “Her Feline Majesty Lilibet, Queen of Historic Pensacola” (a beloved local cat and social media personality known throughout the historic district).

“With most of my art, I try to express an absurdity that will hopefully elicit joy in the viewer,” they said. “There’s a lot of turmoil in the world, especially now, and I like to try to add some gleeful imagery of critters to counteract the stress if only for a minute or two.”

That ethos carries directly into their residency at 309 Punk Project, where Diffee plans to spend the month creating new work and engaging with the community through a series of events. During the upcoming Night on the Tracks—which is a multi-venue event series along the Wright Street railroad tracks—Diffee will host a “Make Your Own Possum” workshop that blends their playful artistic approach with 309’s DIY spirit.

“I want to make the act of creating art more accessible to everyone,” Diffee said. “From doodling on a sticky note to painting a large-scale mural to making a possum out of craft felt sheets. I like being able to provide any tools or advice that I can that will take the pressure off people so they feel free enough to create.”

The workshop includes open studio hours, alongside a free book giveaway hosted by the Sapphic Book Club. For Diffee, the goal is simple: get people making things with their hands, without fear of doing it “wrong.”

“I want people to be excited to make something, anything at all,” they said.

During the residency, Diffee is also working on a series of larger acrylic paintings inspired by local wildlife, including some of the animal ambassadors from Wildlife Sanctuary of Northwest Florida. Their first collaboration brought an animal ambassador from the sanctuary into 309’s space to model for a drawing workshop.

“I’m so fortunate that the sanctuary agreed to collaborate with me,” they said. “And that I get to be the first artist to intentionally bring a hawk into 309.”

The Wildlife Sanctuary of Northwest Florida’s work, rehabilitating injured animals and educating the public, mirrors Diffee’s own interest in shifting perceptions around creatures often dismissed as nuisances.

“They do a lot to raise awareness and appreciation for our local wildlife through their educational programs and markets,” Diffee said. “I hope my residency can do some good and bring more support and awareness to their organization.”

For Diffee, that kind of partnership fits into a larger picture of Pensacola’s evolving creative ecosystem.

“What excites me the most about our local arts community is that it exists and that it’s growing,” they said. “More and more art groups are popping up, from weekly craft nights with your book club to larger artist collectives like The Undergrowth. The act of creating is resistance; it is sharing experiences, it is showing up for one another, it is community care, and I’m so excited to see more of it.”

Most importantly, that growth also makes space for artists to embrace their weirdness.

“With the power of art,” Diffee said, “you can just make a weird little guy.”

Draw Some Birds

WHAT: A bird drawing workshop with Jaime Diffee at the Wildlife Sanctuary of Northwest Florida

WHEN: 12-2:30 p.m. Friday, May 15

WHERE: Wildlife Sanctuary of Northwest Florida, 105 N. S St.

COST: Free, donations accepted

DETAILS: @309punkproject, @wildlifeofnwfl

Night on the Tracks

WHAT: A community-wide arts event organized by 309 Punk Project featuring a night market, live music, a workshop with Jaime Diffee and more

WHEN: 5-11 p.m. Saturday, May 16

WHERE: Old East Hill neighborhood, along the Wright Street corridor

DETAILS: 309punkproject.org, @309punkproject

Jaime Diffee’s Artist-in-Residence Closing Exhibit

WHAT: An art show and fundraiser for the Wildlife Sanctuary of Northwest Florida

WHEN: 5-8 p.m. Friday, May 29

WHERE: 309 Punk Project, 309 N. Sixth Ave.

COST: Free, donations accepted

DETAILS: @309punkproject, @heyletscommunicate