The faces, all handsome, all angular, none smiling, stare right back at the viewer. The way the paintings combine glamour and danger, they might be models’ portraits or mug shots — maybe you feel a little uncomfortable looking at them, because you can’t be sure.
Most people in Provincetown have seen the artist at work on these paintings. On warm nights, Cassandra Complex paints them outdoors on wood panels in front of her eponymous gallery at 244 Commercial St. Using acrylics and a deck of playing cards in place of a palette knife, she lays down large-scale close-ups of men with chiseled features that emerge from dark backgrounds. Some have a boxer’s nose with bandages across the bridge.
The artist’s mother, Janice Flaherty, functions as Complex’s de facto art dealer — and a savvy one at that, engaging browsers in conversations about the works. On a warm September evening, she sits in a lawn chair next to her daughter, sipping her vodka and soda. Flaherty’s fashion grabs almost as much attention as the men’s faces in the paintings. She wears a gold necklace, long gold earrings, bright pink lipstick, and a Cheshire Cat smile.
Flaherty’s second husband, who was like a father to Complex, died after suffering an aneurism 14 years ago. It is his memory that compels Complex to paint men’s faces, her mother says. “He was a strong role model for her,” says Flaherty.
Complex’s last name is Flaherty, too. In a 2014 article about her paintings, the Provincetown Banner incorrectly identified her as “Cassandra Complex.” She thinks they took the name from her old email address. “You know, it means those people holding ‘The End Is Near’ signs,” she says. “I thought it was funny.” She took the name and ran with it.
There is something of a search for identity in Complex’s arrival at making her paintings. She was born in Los Angeles but grew up in Bridgewater.
After dropping out of UMass Amherst in her junior year, she tried to join the Church of Scientology after reading a paper a college friend had written about it. But she didn’t end up joining. “It didn’t take,” she says. Next, she joined the military, but she was discharged, she says, “for failure to adapt.” Then she got a job as an EMT in Lynn, “The city of sin — you never come out the way you went in,” she sings.
The EMT job lost its allure after her father’s death, Complex says. She took a nightshift job watching the cameras at a Stop & Shop warehouse in Braintree, and that’s when she started drawing with pen and pencil at her desk for four hours a night. Eventually, she moved to oil pastels. She painted portraits that looked like her father using her warehouse security cards to make straight lines. When her bosses saw the footage of her painting during her overnight shift instead of going out to check on the warehouse, they fired her.
Complex moved in with her mother and kept painting. She worked from her imagination, rendering heavy-browed, big-nosed, square-jawed, thick-necked men. They were bald because her father was bald, she says. When she talked about getting yet another job, Flaherty says, she told her daughter, “You’re not going to get a job — you’re going to be an artist.”
Flaherty and Complex went around that year talking to gallerists with five or six paintings in the trunk of their green Honda Civic. After one gallerist challenged her to paint three seascapes — not for sale, just as an exercise —Flaherty had the idea to head for Cape Cod with them.
They were turned down by the galleries, though one artist, Gail Browne, offered encouragement. “You’re a good artist,” Browne told her.
“That was huge for me, just hearing that,” says Complex.
Flaherty and Complex came back to Provincetown in the fall and met Patty Deluca, whose Deluca Gallery was across from the library. She invited Complex to be a part of a three-person show the next season. By chance — “Deluca’s horse died, and the other guy couldn’t get his stuff out of storage” — Complex got a solo show, says Flaherty, and sold every piece. Two years later, she began showing her work at the Woodman/Shimko Gallery.
“Sometimes I have a thing where I can see ahead in time,” says Flaherty. “I knew she’d get a gallery.” Complex opened the Cassandra Complex Gallery in 2020. It took her two years, she says, to get the glitter out of 244 Commercial Street in the spot that used to be House of LaRue — Alan Cancelino’s “LGBTQ street to stage” shop.
Out front, Complex finishes a portrait. She repositions the painting, Sometimes It Just Doesn’t Go Your Way, so the crowds on Commercial Street can see. The painting is of a bearded, dark-haired, blue-eyed man with a furrowed brow. He has a widow’s peak — Complex is shameless with the black acrylic.
“I don’t have the patience for oil,” she says. “Or for ventilation.” She paces around the painting in her worn sneakers, a Kamala Harris shirt hanging down to her thighs.
Notes of pink, yellow, and white shine on her subject’s forehead as if he were under the light of a lamp in an interrogation room. The wood panel shows through in places, giving him a texture that looks fittingly tough. Complex says the men’s faces have evolved. They are no longer bald. They are no longer all her father.
In recent collaborations with Eastham artist Chris Kelly, the portraits pop out of patterned backgrounds. Kelly uses acrylic ink and silkscreen techniques on the panels and delivers them to Complex, who paints on top of them with acrylic.
Complex and Flaherty now live in North Truro. “It beats the hours of driving and sleeping at rest stops between Provincetown and Bridgewater,” Complex says. “I put 300,000 miles on my Honda.” When she traded in her car, they asked what she did for a living. “She thinks in the car,” was the answer, Flaherty says.
“I finally found the thing I’m good at, and I like it,” Complex says. Her father still shows up once or twice a year in her paintings, she says. “It’s almost like he’s still taking care of us.”
