I’m sitting in a cramped art studio in Woodberry, trying to find something to focus on. There are almost 30 people in the room, staring at me.

But even more eyes, those in portraits covering the walls, seem to peer my way. They belong to models before me who volunteered for an alla prima portrait. It’s a painting technique in which artists complete their work in one sitting, which, for the people around me, means about three hours.

This is 100 Heads Society, where friends and strangers dedicate Monday evenings to honing their portraiture skills. The group was built on the idea that artists need connection and community to grow, and dedicated time and space to inspire discipline.

The day I posed for a portrait was also celebrating a milestone — the first time two artists painted 100 portraits.

I sat down in the leather chair at the front of the studio and took off my glasses, because they might be a pain to paint. It took me a few minutes to get comfortable.

“Should I keep on my jacket,” I asked Lauren Carlo, who runs the group.

She studied me before answering. “Let’s keep it. It’s a nice blue in contrast with the white and orange,” she said, referring to my top and baggy pants. Then she started the music.

“Let’s begin,” she said.

The forming of a society

For centuries, only the rich, white and powerful — in Europe, that meant royalty and clergy — could commission paintings, said Virginia Anderson, a senior curator at the Baltimore Museum of Art.

An artist’s mark of success was often their ability to draw the human form and paint portraits, Anderson said, but women and people of color were often denied access to instruction even as art schools began to pop up in the 19th century.

Self-taught artists, however talented, struggled to find studio space, subjects and even time, Anderson said. Groups like 100 Heads Society can provide artists with these elements.

In the spring of 2022, Carlo, who studied classic realism at the Schuler School of Fine Arts in Station North, began hosting former classmates in her rowhome basement to practice portraits. The group took turns modeling at first, then started having friends of friends sit. By the end of that year, her space felt crowded.

A series of serendipitous meetings brought her to the Parkdale Avenue warehouse where the group now meets on Mondays. Her now-fiancé, Jon Marchione, had a mutual friend who was looking to share his space.

“It would be once a week. It could be pretty large. It would be a lot of goofy portraits,” she told him. “And he was excited about it. I was shocked.”

Then she ran into an old friend who told her to check the Maryland State Arts Council for grants. She could afford the studio rent and keep the portrait nights free for almost two years. (She only recently started charging $5 to attend, which she hopes is still affordable.)

Since the group moved into the studio in May 2023, it’s only grown. It’s had two exhibits, turning the studio into a mosaic of faces in different palettes and styles.

Nights usually start quietly, as people sketch and the model gets used to posing. Then someone will comment on the music playing or bring up a TV show they watched. Some models chime in, while others try not to laugh. Halfway through, there’s a break to snack on tater tots.

Many artists, including Carlo, are trained with oil paints. Others use these sessions to explore different mediums, from gouache and watercolor to charcoal, markers and digital illustration.

“The energy feels the same, which I’m really happy about,” Carlo said. “Because it started off with friends, like people who really knew each other.”

‘Just bring four colors’

Sara Autrey felt nervous modeling for the group. She was a last-minute replacement, and there’s a lot of room for interpretation on how you look, she said. But the portraits felt “very sincere,” she said.

“What an honor it is to ever have somebody put paint on paper and put your face on paper,” said Autrey, who owns the North Baltimore thrift store Get Shredded Vintage.

She realized she was more like a “helpful tool in their artistic process,” she said.

“Not to sound like a fridge magnet, but every person is art in their own way,” she added.

I told Autrey I attended my first 100 Heads night last year after seeing the portraits from that night. She had posted a photo of herself on social media surrounded by the portraits, where she’s wearing red devil horns.

Despite knowing no one was judging my artwork, I felt embarrassed by my attempt. I didn’t know how to paint then, I told her, and I’ve never had formal training.

Neither did her boyfriend, Eugene Golovin, she said.

Golovin began painting after a back injury left him temporarily out of his usual hobbies, including swing dancing. He asked Carlo, whom he met at Mobtown Ballroom, how to get into painting.

“Just bring four colors of paint,” Golovin remembers her saying. Yellow ochre, warm red, ivory black and white, known as the Zorn palette.

Golovin felt intimidated his first night in Carlo’s basement, sitting next to Marchione and Jon Schubbe, who are trained illustrators.

But his first portrait wasn’t bad, Golovin said. He got the complexion right, the face shape, too. Every week, he talked to the artists around him: How did you do this? What were you thinking? How did you get to this color?

He switched up what he wanted to focus on or tried a new concept every week. He learned to filter what he saw as a painter, squinting as he looked at the model and refraining from painting every fold of the skin. He learned to treat the head as a cube, then draw in the features, carving it away like a sculpture.

Then, two years and several months later, he was the first person to complete 100 heads.

The ceremony

When Carlo realized Golovin and Marchione were close to completing 100 portraits, she started planning a ceremony. She wanted to lean into the secret society-esque name of their group. It happened the same night I sat as a model.

The studio is usually unlocked, but Marchione didn’t open the doors until after 6 p.m.

The tall windows were covered and the lights off. Chairs were arranged in front of a makeshift podium. A neon red light strip formed the number 100 on the wall, and lamps were spread across the studio, illuminating decorative skulls on the shelves.

Carlo and other longtime members wore dark robes and Victorian-style masks, standing straight-faced as people walked in, laughing as they took in the room. Marchione and Golovin walked to the front row, and Carlo opened a large book, placing it on the podium.

“If ye wish to obtain greatness in the realm of portraiture, partake in the practice of studying the portraits, once every Monday, until ye has reached 100 portraits reduced in total,” she raised her voice dramatically, enunciating words as if reciting from ancient texts.

“All rise to Eugene Golovin and Jon Marchione,” one of the robed members said. Golovin and Marchione were told to kneel.

“These recruits must first partake of the sacred tots,” another said. “Perfectly cooked and crunchy, it gives our society the power to complete our hallowed test.”

After being fed tater tots, Golovin and Marchione were handed custom-made rings inscribed with the group’s name and mascot. People burst out laughing and clapping.

The lights went on, and they started to rearrange chairs. That was my cue.

The first 10 minutes were excruciating. I became too aware of how my eyes moved, how much I blinked. I had a laughing fit when the soundtrack for “KPop Demon Hunters” played, so Carlo switched to more mellow music.

I tried to let my mind wander. I listed songs in alphabetical order in my mind to pass time. But I would move my body without realizing or make faces depending on what I was thinking.

By the third break, however, it almost felt like a dream. I relaxed my gaze, my surroundings becoming unfocused. People chatted around me about ABBA, Gracie Abrams and Taylor Swift, along with a Twitch show run by someone’s partner in which they watch random videos — including an hourslong lecture on types of fowl.

I was only half-listening, but it was the most grounded I felt in months.

My back ached by 9 p.m., and my legs fell asleep. I walked around during the breaks and peeked at people’s artwork. I asked them about their process and what they were focusing on — one artist was inverting colors to try a cooler palette, while a painter behind her used mainly red tones. One person said they had been working on my eyebrows for several sessions, another on my nose.

(A couple of people said I had “lovely features” and was “very fun to draw,” so I will be riding on that high for the foreseeable future.)

Once I saw all the paintings and drawings together, I audibly gasped.

I now understand what Autrey meant about being a tool for artists. It’s somewhat of a transaction — some of the artists donate their work to thank the models; others sell the paintings. But it’s also about connecting, allowing yourself to be seen and studied.

I came back the following Monday, this time to paint. I chatted with one of the artists, Andrea, who had painted a portrait of me. Before we went back to our canvases, I told her it was nice to meet her.

“It’s nice to meet you too,” she said, and then she paused. “Well, I feel like I already know you.”