Speaking with Ruby Pearl

Ruby Pearl entered her first art competition at the age of four.

“Come to find out, I won first prize. The thing is, they didn’t know I was a little girl.”

It was not, Ruby hastens to say, a children’s art competition. The winning piece was not a stick figure.

It was a painting – a street scene. On the left side of the painting, pedestrians and cars moved about on a summer street. On the right side, the same scene, but shrouded in winter.

Ruby has considered herself an artist ever since that first critical success, and over the years, her work has earned praise and acclaim. Her pieces are displayed at openings regularly – she reels off nearly 20 exhibitions and events just in the past few years, including an opportunity to display her art at the White House. Ruby makes a stable living selling her work. She is working on a piece right now on commission: a group of women smiling.

By all accounts, Ruby is an extremely successful artist. And as she has found success in her art, she has moved toward a place of peace and stability in the face of mental illness, bouts of homelessness and despair, and abuse at the hands of her family members.

Painting Women

Ruby’s latest commission – a work in progress, the group of women smiling – is unusual. It is rare for her subjects to smile.

Ruby paints people, usually women. She’ll paint men on commission, but she’s always painted women.

On the women who appear in her work, Ruby reflects. “They are walking through life calmly in their solitude.”


They are living their lives. They are not posed figures, but rather, real and alive.

Not long ago, a man at an opening asked her why she only paints women. It was less of a question, Ruby remembers, and more of a statement.

Why do you paint only women.

Ruby didn’t have a ready answer. Fortunately, some other guests were trying to get her attention at that moment. So she turned away, and the man never got his answer.

Since that encounter, Ruby has considered the question. Painting women had always seemed so natural. Why does Ruby paint only women? She had never thought to ask herself that.

Ruby often slips into the third person when she speaks, as if describing a close friend. “Why does Ruby paint only women?”


A few minutes later, I ask the same question again, because – and the irony is not lost on me – I never got a clear answer. Ruby is tickled by my persistence. She smiles, and begins.

“I’ll reiterate.”

Her smile grows wide and gentle.

“I paint women because I feel as though I’m painting myself.”

She speaks of expression, realization, and affirmation.

“My soul speaks to the image that I’m painting.”

When Ruby paints, she communicates with “the little me.”

“The little me?”

Ruby has recently discovered this part of her soul while making peace with her past.

“I don’t think I recognized her until two years ago. I started writing, I write journals, and then I started talking, little me, little me.”

The “little me” was an epiphany for Ruby. Her art became collaborative in a new way, inspired by this aspect of her being. Ruby brings life to her “little me” by painting.

“It’s recreating the little me, something beautiful. Solitude. Calm. Loving.”

The Embrace of Gateway Arts

Ruby first arrived at Gateway Arts 20 years ago. At the time, she was homeless, depressed, and moving on from a failed marriage. She often felt overwhelmed by suicidal thoughts. She suffered from post-traumatic stress, bipolar, and anxiety disorders. At a low time, Gateway welcomed Ruby and supported her.


“I got through it thanks to Gateway. If I didn’t have Gateway, I might not be living or breathing. Gateway has given me a purpose to live for the first time. By finding a home of my own for the first time, I found calmness and solitude of my own.”

She remembers how Gateway held her close and safe. To this day, the Gateway staff can see when she is having a hard day. They ask how she’s doing, which she appreciates very much.

As Ruby and I weaved through the artists and works in progress at Gateway, everyone seemed to know and have something to say to Ruby.

“Hi, Ruby.”

“Ruby, you around later?”

When Ruby arrived at Gateway, she knew no one.

“They took my hand, they sat me down, they gave me supplies and a sense of being!”

“I didn’t understand what Gateway was. All I understood was that I’m really unhappy and I will do some drawing and they handed me some paints, and I drew these big, dark images.”


Today, her fellow artists and friends feel her serene, loving, strong presence as she moves through the studio. She is surrounded by art, creation, and friends.

Her Art Emerges From Struggle and Peace

Ruby’s artwork and the challenges she has faced are inseparable. Through her art, she has found escape from the difficulties of her illness, and her art has been shaped by her thoughts, fears, and struggles.

As a young child, Ruby was most comfortable alone with her painting supplies.

“I never was without supplies. I had canvas boards, I had paints, I don’t think they thought of giving me acrylic.”

Her parents were very supportive of her artistic ability and passion.

“Most of my friends or family would be out doing their thing, but I was very withdrawn. My enjoyment was not to be with other people or have a good time or whatever. Mine was being in my room or the living room doing my art.”

It wasn’t until well into adulthood, in her early 40s, when Ruby sought treatment for her mental illnesses. In the process of diagnosis, she also realized that her troubles were connected to the abuses she suffered at the hands of her parents. From an early age, Ruby’s father sexually abused her, and her mother tormented her with verbal abuse.

Today, Ruby manages her illness through a positive attitude, support from friends, fellow artists, and staff at Gateway, prescription medications, and weekly therapy.

The pills are a sticking point that she takes care to explain. Ruby was hesitant to use pills to treat her illness. As a child, her mother told her that she shouldn’t take any medicine.

“I asked my doctors, ‘How can a pill help something that’s permanently inside me?'”

But the doctors convinced her to try them, pointing out that she could always stop.

“It took them about three months to convince me to at least try it. When I tried it, it was like tears of joy.

“They were right. It really made a huge difference.”

Ruby Pearl’s Style

Ruby relishes in trying new styles, and she intentionally defies categorization.

“When you see a Ruby Pearl painting, it is hard to decipher what else might be a Ruby Pearl painting.”

Her style depends on her mood and what is most interesting to her at the time. This can be seen in her work.

Sometimes Ruby experiments with mixed media, as in the metal circular objects that emerge from the wild hair of a woman in motion whose steady gaze falls forward and beyond the viewer. She does not shy from abstraction, and her work features elements that are strikingly realistic. Ruby may paint with broad, bold strokes, or perhaps with points and little dots. It just depends on how she feels.

And women. Ruby Pearl paints women, and she begins with their eyes.

“Their eyes are going to specifically tell me who these women are going to be on the canvas. I create a relationship with these women emotionally, speaking to them.”

In their eyes, Ruby can see that the women will not judge her.

“These people that I paint want to be in my life. They want to talk to me, they want to tell me their story.”

“They’re part of who I am.”

Looking Forward

After so many years at Gateway Arts, Ruby has come to accept her struggles, illness, and creativity as all parts of who she is. In fact, she is happier than she’s ever been before – whether or not she’s smiling.


“The older I get, the most unbelievably happy I am.”

“I’m moving forward. I’m learning to say, bye, I don’t know what’s back there. I only learned to do that in the last few years.”

Ruby’s work continues to be featured in the Boston area and beyond as she paints from her studio, with her friends, at Gateway.