The art collection of Ellen and Sherwin Waldman has thoughtfully grown as they transition through different stages of their life. From Al Hirschfeld to Keith Haring, the eclectic mix of pieces represents who they are.

Photographs by Jon Cancelino

Ellen Diamond Waldman in the dining room of her Highland Park home.

Ellen Diamond Waldman began developing her artistic tastes when she moved to Paris after graduation. During her time on the Continent, she loved perusing the French flea markets for clothing, and, though she claims she wasn’t artistically inclined at the time, it was through fashion she first expressed herself. As she transitioned into different stages of her life, her manner of expression has changed and grown.

After completing her graduate work, she took a job at the School of the Art Institute of Chicago as the school psychologist. Meanwhile, she was also settling into her first home. Working in such an artistic setting, she began trusting her tastes and actively collecting pieces to complement her home. Now that she and her husband, Sherwin Waldman, are empty nesters with their three children out of the house, Ellen has moved onto another stage where she is actively making her own art. She took a mosaics class about eight years ago and has been hooked ever since. “It’s like this whole side of me came out in my 50s,” she explains. “Women put a lot of nurturing energy into their families. When the kids need you less, that energy goes somewhere. In my case, it went into creative pursuits.”

Over these stages, the Waldman’s art collection has thoughtfully grown. As Ellen walked through her house, each piece she pointed out had some personal story or reasoning behind it. “Everything was bought or given to us with love,” Ellen says. “It all has meaning and sentimental value.” She first stopped in front of the clay-colored fireplace where an Al Hirschfeld pen and ink caricature of George Harrison proudly hangs above the mantle. Hirschfeld was famous for his satirical portraits of celebrities and Broadway stars and was commissioned by The New York Times, where Ellen grew up seeing his work. As a big fan of the Beatles and a yogi herself, when she came across the caricature at the Highland Park Art Center’s Recycled Art Sale, she immediately put a bid on it.

Roy Lichtenstein's "Shipboard Girl"

Next was the instantly recognizable Roy Lichtenstein print. The 1965 piece, entitled “Shipboard Girl,” was a gift from Ellen’s parents who purchased it at a silent auction in New York. “They loved art and collected a number of pieces and had a huge art book collection,” Eileen remembers. Also in the den is another print from renowned New York artist Keith Haring. Ellen and Sherwin purchased the print from one of their many visits to New York (where Ellen grew up). They went to Haring’s Pop Shop in SoHo and were lucky enough to meet him and have him sign their print. “All his stuff was for sale, which was part of that pop notion to demystify art as elite and instead made it commercial and accessible,” Ellen recalls. “I recognized Haring the moment I saw him and explained that I was a big fan, so he offered to sign our poster.”

Piece on the left by pop artist James Rizzi

Ellen and Sherwin also met another SoHo artist upon one of their visits. They both admired the work of pop artist James Rizzi. “His work was so exuberant and really urban,” Ellen says. She got in touch with the artist to purchase one of his pieces, and he invited the two of them to his studio where they ended up spending the whole afternoon hanging out with Rizzi and his girlfriend. “I thought he’d kick us out, but he was very friendly,” she retells. “My husband and he got into this big conversation about golf, which is the last thing you would expect from this SoHo artist.”

She then walked into the spacious dining room where a massive dining room table stands in the center of the room—perfect for a family Thanksgiving. Over the hearth hangs a modern twist on a traditional Japanese wood block print. The turquoise and orange portrait is superimposed over the New York City skyline. The combination of her travels to Japan and her parents’ view in New York made the piece very poignant for Ellen.

The Waldman's diverse mask collection

While dining, many guests’ eyes are attracted to the east wall where two rows of masks gaze upon the room. The collection of eight masks is actually a greatly edited version of what the Waldmans previously had. “I got into them because as psychologist, I studied Carl Jung,” Ellen says. “He has a whole concept of the persona—that’s the mask that we wear when we go out into society. That’s why the mask collection grew and I was fascinated with that concept.”

Each of these masks, like all of their pieces, has a certain memory behind it. The Japanese mask in the center, painted in gold and black, was Ellen’s first. She bought it as an exchange student in Japan during high school. The oblong red and black mask on the far right was from Kenya, the country that actually brought Ellen and Sherwin together. Ellen spent some time in Amboseli, Kenya, babysitting biologists’ children during the summer. She had known Sherwin through her undergraduate work, and he was sent there for his final semester of medical school. “He called me up and we went out to discuss what I knew about Kenya, and we’ve been together ever since,” she says with a smile.

Though the Waldmans have been living in their Highland Park home for almost two decades, Ellen adores her art collection’s ability to continuously engage her. “Even for me, though I live here, I can always find something new to delight my eye,” she says.