How a Haunting Alabama Upbringing Shaped the Art of Donny Finley

Picture a young boy in rural Alabama in the 1950s. Dirt roads. No indoor plumbing. Farmland rolling to the horizon.

The boy is sensitive, reflective. He spends much of his time—after school or when his parents are working—with his grandmother. She sits and quilts and tells him tales of her life in their native Clay County, of family and church potlucks and sing-alongs. She also talks of a devastating tornado and, later, of a gruesome triple homicide. The boy listens to her, quietly, attentively, as he lies on the floor and sketches images out of an old Sears catalogue.

For a time, when the boy is four or five, his father is a policeman, and the family lives in the county jailhouse in an apartment below the cells. The boy sees all types of people come through: thieves; bootleggers; a kindly, smiling woman who hands the boy and his sister candy through the bars she’s stuck behind because she has recently murdered her husband.

The inmates yell and make noise at all hours, and when it gets to be too much for the boy, he walks outside to a patch of grass between the jail and a barbed wire fence. The inmates lean out of the cell windows and call to him. He blocks out their voices as he lies down in the grass to look up at the sky, watching the clouds continuously shift into different formations. He does this for hours at a time.

Now picture this: Some six and a half decades later, the work of the artist Donny Finley—watercolors, egg temperas, oils, and acrylics, running the gamut from realism to impressionism to vignettes from his East Alabama childhood—has won major awards and been featured in the White House. His pieces have hung in galleries in New York, Nashville, and New Orleans, and on the walls of musicians and movie stars and private equity investors. He has been compared to the iconic regional realist Andrew Wyeth, one of the most renowned American artists of the middle twentieth century. “I think Finley is a genius with his ability to conjoin colors and paint shadows and light,” says Peter Weller, the RoboCop actor who has a PhD in art history from UCLA. “He’s a game changer as far as American watercolorists go. And I’m not saying that because I own some of his paintings. I’m saying that because that’s how I felt when I bought them.”

To see Finley now—a seventy-three-year-old in a blue oxford shirt and pressed khakis, with neatly combed white hair and intelligent green eyes behind wire-rimmed glasses—you’d never know about the tornado or the murders. Sitting in his art- and book-filled home in Greystone, a well-to-do golf community on the outskirts of Birmingham, Finley hardly resembles that lonely little boy, but his serene paintings surrounding him in his home studio tell the story in their shadows. He’s never strayed far from that childhood in Clay County.

Finley’s grandmother Dessar Davidson was a central figure in his life. After she met and married Finley’s grandfather, he was bootlegging whiskey, and Davidson threatened to turn him in to the authorities. He then found salvation, to the point that he insisted on hosting the circuit preacher at their home one Sunday. As the neighbors gathered, a tornado touched down from out of nowhere. Davidson instinctively grabbed Finley’s mother, who was then a toddler. The two ended up in a nearby field, still holding on to each other. Davidson had nails in her legs and no recollection of what had happened. People and pieces of her house littered the landscape. They found the preacher dead beneath the rubble.

Years later, when Finley was eight, he awoke one morning to the sound of his grandmother shrieking. She’d just learned that her sister, her niece, and her sister’s mother-in-law had been brutally stabbed to death overnight in her sister’s home down the road. The sister’s fourteen-year-old grandson had murdered them, supposedly after they’d refused to give him money for new football shoes. He would go to prison. Upon his release, he would murder two more people, go back to prison, escape, get caught again, and eventually die on death row.

Tornadoes and storm cellars and murder haunted young Finley’s life and dreams. Afraid to live by themselves, his grandparents sold their home and moved in with Finley’s family across the street. “My grandmother would tell me these stories, and I would lie awake at night thinking about them,” Finley says. “It affects you, the way you see. When I started painting, I thought about these things and my grandmother. She was the first person I started painting.”

Back then, Finley’s sole exposure to art came from browsing encyclopedias. “There was one painting I saw in an encyclopedia that always stuck out to me, of a young boy in a rural setting standing in a doorway, sort of looking out, maybe at the sky,” he says. “I saw myself as that boy, thinking about what I would become.”

When he enrolled at Jacksonville State about an hour outside of Birmingham, the school offered a few introductory classes on the subject, but no art major. Finley could never shake the inspiration he’d found in those old encyclopedias, though. After attending a local art show, he felt he might be capable of producing something worth displaying and selling, too; he started painting in earnest during his junior year. “I’d be sitting up in my frat room painting while the other guys were partying,” he says.

A few people told him that his paintings looked like Andrew Wyeth’s. Curious, Finley went to the college’s library and found a book about Wyeth. “I opened it up and there was that painting of the boy I’d seen in fifth grade,” he says. (The painting: Wyeth’s Albert’s Son.)

Soon, he began traveling the South to sell his work—mainly watercolors then—at outdoor shows. When classes prevented him from attending in person, his parents and grandmother went in his stead. He made several hundred dollars a weekend, which helped him pay for college. Though he graduated in 1975 with a degree in business, Finley decided “to give my art a year and see how I did.” He went to more than forty shows that year and made enough to justify his career choice, but not quite enough to afford the down payment on a house in Birmingham for himself and his soon-to-be wife, Janet. At a show in Dothan, Finley hit a wall. “No one came by to look at my art,” he says. “I sold one painting for fifty dollars and one print for thirty. I felt really discouraged, and I had to get ready for a show in Georgia the next week.”

A moment of serendipity followed, one of a few that have struck Finley during times of need in his career. As he packed for the Georgia show, he received a phone call from a man in Tennessee named Fred Webber. “He said, ‘You probably don’t remember me, but I bought a painting and a print from you last weekend,’” Finley says. “I remembered him, of course, because that’s all I sold!” Webber asked Finley to come to Nashville with some paintings. Finley told him thanks, but that he couldn’t because of the upcoming show, and the conversation ended.

Webber called back a few minutes later and told Finley that if he came to Nashville, his friends would throw a party for him. Those friends? The country singers Jerry Reed and Ray Stevens. Finley packed his camper truck with eighteen paintings and headed north.

“I drove up there, and they all came out and greeted me like I was a long-lost relative,” Finley recalls. He sold sixteen paintings on that trip and gave one to Webber as a thank-you. “And I had the down payment on my house. My life has been like that a lot.”

The appeal of Finley’s early work, by his own estimation, came from the fact that he painted “real life,” which stemmed from the time he spent with his grandmother. “When I first started going to art shows, everyone was painting flowers and barns,” he says. “I was painting figures and quilts and storm pits, and the things I knew, the personal stuff.” Still today, behind Finley’s clean, bucolic paintings lie suggestions of contemplation and solitude. They often contain a hint of darkness somewhere off the canvas, unseen but felt. Even when he tightens his aperture, he always leaves space, in the skies and in the light they cast. For collectors like Weller, an accessibility defines Finley’s work. “I feel like I can walk into his paintings,” he says. “Like I’m almost in the thing.”

Shortly after selling his art to Reed and Stevens, in 1979, Finley signed with a gallery that had locations in New Orleans and Jackson, Mississippi, and he stayed with it for a decade. During that time, his reputation grew. His paintings soon started to fetch five figures. The gallery paid him a salary and, every once in a while, a small share of profits, instead of a per-sale commission. “I didn’t make a lot of money, but it was great to be able to develop my art,” he says. “I had the freedom to try anything I wanted.” He began to work with egg tempera, a more time-consuming and difficult medium that he loved because of the way it depicted light and shadow. He went back to the oils he’d toyed with in college and experimented with acrylics. In the mid-1980s, Finley painted his grandmother, wife, and daughter on a wooden egg. The White House featured the piece during the annual Easter Egg Roll.

He and Janet traveled, seeking inspiration. They visited the coal-mining towns of West Virginia, the banks of the Mississippi River, the swamps of Louisiana, coastal Maine. Finley would take hundreds of photographs and render sketches of what he saw. Even with this broadened geography, his paintings maintained a regional feel, and he never lost sight of what he saw as his mission as an artist. “What I’ve found with painting is that it’s not about pleasing the masses,” Finley says. “You just have to reach that one person, to strike a chord.”

Around that time, Finley’s work struck just such a chord with Tom Windham, a Mississippi-born neurosurgeon, and his wife, Linda. The duo had stopped in at the Jackson gallery and noticed a Finley watercolor called Creek Fisherman. They bought it on the spot. “It’s still hanging where I can see it now,” Linda says.

The purchase was a blessing for Finley in more ways than one.

The Windhams, as it turned out, would play a central role in helping him emerge from the darkest period of his career.

As Finley neared forty, he began to have concerns about his contract with his gallery. He was locked into a fixed salary, even as his paintings fetched higher and higher prices. He sold prints to supplement his income, but he felt the arrangement was no longer equitable. He had three daughters and bills to pay. He had also received an offer from the Birmingham investor Temple Tutwiler to rent an affordable space above the restaurant Bottega where he could have his own studio and display his work.

With all of that in mind, Finley chose not to renew his contract. The gallery still owned some of his paintings, though, and decided, in turn, to sell them at a discount, which made it much harder for Finley to sell new paintings for what turned out to be years. “I understand that they made a business decision and that they had their own bills to pay,” he says. “But it just broke me, spiritually and financially.”

After the first few months of no sales, the Finleys’ savings had drastically dwindled. “Janet prayed about it, and she said she thought we were supposed to give away most of what little money we had,” Finley says. He wasn’t quite ready to go that far, so he gave a hundred dollars to someone in need. Nothing changed. The bills piled up, and he still couldn’t sell a painting. “I finally said, ‘Let’s give away more,’” leaving the couple with nearly nothing.

Finley felt bad for the people who had once paid top dollar for his work, and who now saw his paintings selling at a discount. Among them: the Windhams, who had previously bought a piece for $20,000. When Finley called them to apologize, they were very understanding. In fact, they were coming to Birmingham and wanted to take Janet and him out to dinner. Finley accepted. After the meal, the Windhams visited Finley’s studio and bought a painting for $15,000.

The windfall helped, but for the next few years, the discounted paintings continued to surface and affect his sales. Then one day amid all of this, Janet asked Finley if there was one thing that he’d always wanted to do. “I said, ‘Go to Italy,’” he recalls, “but I knew we didn’t have the money. Janet said, ‘Let’s go anyway.’” So they did. They sat in Venice’s Piazza San Marco at night and listened to the musicians. They visited out-of-the-way spots, such as Venice’s Jewish ghetto and the cisterns beneath Siena. “I came back so energized,” he says. He began painting “like crazy,” staying up all night, going to bed at 5:00 a.m., and then waking up four hours later to resume. Soon, he had enough work for a solo show. They set it for March 12, 1993. “We put all the money we had left into it,” Finley says.

Fate had other plans. The evening of the event, a blizzard that would come to be known as “the storm of the century” hit Birmingham, dropping more than a foot of snow. No one came to Finley’s show. He and Janet decided to try it again a week later, on a Sunday, and ran a small ad in the newspaper. This time, a packed gallery greeted Finley upon his arrival. “I think people were excited to get out after being stuck indoors for so long,” he says. It became his most profitable show to that point.

His career back on track, Finley began working with galleries across the country: on Cape Cod; in Chevy Chase, Maryland; in Jackson Hole, Wyoming; on Park Avenue in New York. DeBruyne Fine Art in Naples, Florida, championed his work for a decade. (The numerous galleries carrying his work these days include West Lives On Gallery in Jackson Hole; Sportsman’s Gallery in Charleston, South Carolina; and Beverly McNeil Gallery in Birmingham.) In 2006, the captain of the U.S. Ryder Cup golf team commissioned Finley to paint a father teaching his children to fish on the river that ran through that year’s competition course, illustrating the legacy the players were leaving behind. His work won awards from the American Watercolor Society, the National Academy of Design, and the Salmagundi Club. He even reconciled with his former gallery.

Finley also started to take on more commissions. A Wisconsin couple, Terry and Mike Wickman, hired him to depict their house in Green Bay. “My parents saw it, and then they commissioned Donny to do a painting of their house,” Terry says. Weller, the actor and art historian, commissioned a portrait of his grandmother. “It makes me weep when I look at it,” he says.

Very few of Finley’s fans own just one of his works. Weller has four and is keen to buy more. When Temple Tutwiler lost his three Finleys in a house fire, he promptly bought four more. The Wickmans own eighteen. Tom Windham died in 2021, but Linda still owns more than twenty. “I recently downsized and sold a bunch of art,” she says. “But I did not sell any of my Finleys.”

What seems to grab Finley’s patrons are the stories his works tell. “Our first painting of his was of four aprons hanging on hooks in what looked like an old-world kitchen,” Terry Wickman says. “That was very personal to me. It was exactly what our Christmas looked like, with my mother’s, my aunt’s, and my two grandmothers’ aprons. I thought, ‘Oh my goodness, someone has lived my life!’”

One of Linda Windham’s favorite Finleys depicts one of his daughters and is called Catie Praying. “People always think it’s one of my kids,” she says. “For a long time, Donny couldn’t keep the paintings he’d done because of his contract. I’m not ready to let this one go, but my kids know that when I die, it goes back to him.”

Much as he loves the process of painting and the thought of the finished product hanging proudly on a patron’s wall, Finley remains motivated by the spark that gives each one life. “I’m inspired when I see light shifting across an object,” he says. “I’m inspired by dreams.” Wyeth, Thomas Eakins, and even Vincent van Gogh have also influenced him. “I love that van Gogh told stories through his paintings,” Finley says. “You always knew exactly what was going on in his life.”

Finley’s past, too, continues to sway his work, no matter the subject. A recent watercolor, for instance, depicts an old Venetian building with two clotheslines draped from windows. In an adjacent window looms the figure of a woman. “When I first saw this scene, it reminded me of my grandmother’s clotheslines,” Finley says. In another work called Wedding Ring, his grandmother perches in a doorway with a colorful quilt across her lap. From beneath her sun hat, she gazes out of the frame toward a wash of morning light.

He’s also painted an egg tempera featuring a young woman hanging a sheet of Irish linen on a clothesline as a flock of blackbirds crosses the clouded sky behind her. The young woman is Finley’s daughter Sarah, and the linen hearkens back to those days he sat with his grandmother and listened to her stories as she sewed. “Donny has never left his roots in any way,” Terry Wickman says. “Personally, or in his art.” Though decades have passed, and the circumstances of his life have changed rather dramatically, Finley is still very much that boy lying in the grass in Clay County. He’s still staring up at the clouds, daydreaming.