It’s a lot easier to paint a landscape than to paint a portrait.”

Lenny Karp

Death is unavoidable. The grief that follows for loved ones can be raw, unpredictable, and overwhelming. People cope in different ways: some break down in tears, others scream in frustration, while some bury their pain deep inside. The five stages of grief aren’t always linear or easy to navigate. In Westport, when words fail, some people turn to art, seeking out a local artist to create a portrait — a personal keepsake to honor their grief. 

Since retiring from the furniture retail business, Lenny Karp, a Westport resident, discovered a new passion for painting. His work has evolved into a unique form of healing, one that helps others cope with loss. 

Karp began painting portraits for people who had lost loved ones, including pets, several years ago. He sees it as his way of “giving back” for the blessings he’s received in his own life. 

While Karp has kept the details of the portraits private, he shared that the process takes around 15 hours from start to finish. People who request a portrait typically send him a photo, which Karp then recreates into a painting. He personally delivers the finished portrait, usually in a quiet location like a library. “I meet them in a quiet place, and almost everyone gets emotional,” he said. 

The act of keeping it private is done out of respect for those who are grieving a loved one. Karp explained, “They almost always cry when given the portrait.” This is why he meets them someplace semi-private to offer them a space to grieve the portrait of the life seen in his art.  

A new passion forms in retirement 

Karp, now 82, began his artistic journey at the age of 66 after retiring. “The week I retired, I was browsing in an art supply store and saw a magazine featuring portraits of people with various facial expressions. I bought the magazine and tried to replicate the portraits,” he recalled. 

Lenny then joined the watercolor society in Pawtucket, Rhode Island, where he took classes and formed weekly painting groups. He later joined the Portsmouth and Westport art clubs, entering art shows and refining his skills. Six years ago, he switched to oil painting and now works exclusively in oils. Though he hasn’t limited himself to painting portraits, he has dedicated much of his time to perfecting the craft.

“It took me almost 10 years to learn to paint someone’s face well,” Karp said. “It’s a lot easier to paint a landscape than to paint a portrait,” he went on to explain.

His toughest critic is his wife, Patricia. “Pat has a great eye for detail,” Karp said. He does not sign his paintings and considers them finished only after receiving his wife’s approval. “If she doesn’t give the okay, I keep working on it,” he laughed.

Karp has now painted more than 100 portraits. He’s committed to continuing, as he believes that it’s never too late to find a passion. “Art degrees aren’t necessary,” he said. “With books, magazines, and YouTube, there are many ways to learn. Old-fashioned effort and sticking with your dream also helps,” he went on to say.

For Karp, the act of painting portraits for those grieving is more than just an artistic endeavor; it’s a way to help others find peace through art. His portraits provide comfort, offering a quiet, personal space where grief can be acknowledged and honored.