Let’s begin with the devil.
The object in question is a doll made by Mary Flannery O’Connor sometime in the 1930s. It wears a plaid shirt, a long black cape and a broad-brimmed hat. Its face is painted red, of course, with a big nose and blue eyes. Its most notable feature may be its two left feet.
Now let’s look at the eyeball. A painting of oil on wood, it depicts the various elements of the eye, such as the cornea, the iris and the vitreous humor. It dates from sometime between 1938 and 1942. Perhaps young Mary painted it for science class.
Both objects are on display at a new exhibit on the art of Flannery O’Connor at Andalusia, the farm in Milledgeville, Ga., where the novelist and short story writer lived much of her life. And both could serve as keys for understanding the lifelong preoccupations of this most intriguing figure, who was born 100 years ago this past March.
“My subject in fiction is the action of grace in territory largely held by the devil,” O’Connor once said. She wrote to help people to gain a different kind of vision, often using violence or death to shock the reader. As she once famously remarked: “To the hard of hearing you shout, and for the almost-blind you draw large and startling figures.”
But before she wrote, she drew.
She drew cartoons as a young girl: women with big noses, hats and freckles, women speaking or smoking or giving you side-eye. In college she designed linoleum cuts for campus publications, drawing a following for her spiky sense of humor. And as an adult, isolated by illness, she took to painting in the long afternoons at Andalusia, applying paint impasto with a scalpel so she didn’t have to wash brushes.
She painted landscapes and animals and still lifes and once, notably, herself.
These paintings from her adult years (21 in total) are now on view at a newly built “interpretive center” in Andalusia. They are joined by cartoons and juvenilia that were recently discovered in a family home in downtown Milledgeville. Viewed together with Flannery O’Connor: The Cartoons (Fantagraphics Books, 2012), they offer another way to take the measure of a woman who took the measure of our souls.
The Student
In Ethan Hawke’s film “Wildcat,” the story of Flannery O’Connor begins in the Iowa Writers’ Workshop, where she met the poet Robert Lowell and began writing her first novel, Wise Blood. This is the standard account of her early years. But it is notable that she went to Iowa to be a journalist, following up on her years as a successful cartoonist in college.
What appealed to her about cartoons?
From her early drawings as a child, we can see that she enjoyed drawing people (often her relatives) in exaggerated ways. These are not the freaks and misfits she would later become known for in her fiction, but they do show us a young woman looking at life askew. I am sure some of her relatives did not like these portraits; they are not by any description flattering. But they don’t come across as cruel. Instead, we see a young woman using art to relate a vision of the world—and maybe trying to get a sense of herself.
These paintings were found in the attic of the Cline Mansion in Milledgeville, where Flannery lived during her high school and college years. Through her mother, Regina, O’Connor had deep roots in the city, and her cousin, Louise Florencourt, owned the home until she died in 2023. The house is now full of family belongings that need to be catalogued by curators.
In June I visited Milledgeville to view the art exhibit at Andalusia and explore the city. I stayed down the street from the church where O’Connor attended Mass every day, and on the last day of my visit I was given a tour of the Cline Mansion. The house is adjacent to Georgia College and State University (formerly the Georgia State College for Women), and next door to the former governor’s mansion. (Milledgeville was the capital of Georgia from 1804 to 1868.)
O’Connor and her mother moved into the house in 1938 when she was in seventh grade. The house was run by Regina’s oldest sister, Aunt Mary Cline, who lived there with her sister, Katie, and an aunt. Notably, Flannery was the only child living in the house. One can imagine her escaping to the upper floors to paint or read while her relatives entertained around their large dining table.
What did Flannery, an only child, make of this house full of women? (Her father visited on weekends since he worked in Atlanta; he died of lupus in 1941, when she was 16.) Sharp-witted, she named her Aunt Katie the Duchess, after a character in Alice in Wonderland. Indeed, she had a talent for satirizing her family; at age 10, before moving to Milledgeville, she wrote a series of comic vignettes titled “My Relitives” (sic) that “was not well received,” she later recalled. Her early paintings employed the same comic touch, which was often directed at women.
In these works you can start to see a style that fully matured in her writing. Pick out one or two aspects of a person’s appearance—lopsided eyes, raised eyebrows—as a way to draw the viewer’s attention. One thinks of Bailey’s wife in “A Good Man Is Hard to Find”: a “young woman in slacks, whose face was as broad and innocent as a cabbage.”
The Cartoonist
O’Connor matriculated at the Georgia Women’s College in the summer of 1942. It was not Milledgeville’s most notable institution—that honor belonged to the sprawling State Hospital a few miles away, once called the Milledgeville Lunatic Asylum. But the school did “provide the town’s grace notes,” writes the biographer Brad Gooch, “a steady supply of male and female professors.”
One might expect a bright young woman to fit right in. But like many undergraduates, O’Connor liked to question convention, and the college and its traditions became a target of her pen—or more accurately, her knife. In the pages of campus newspapers, she became known for her linoleum cuts, a method of print making in which a drawing is cut into a sheet of linoleum fastened to a wood block and then printed onto a page with ink. Linoleum cuts did not allow for nuanced detail, but they could be done quickly on a print deadline. They also had to be composed in reverse so they would appear on the page correctly after the printing process.
Once again, Flannery was looking at life askew—composing art from an unexpected angle. She was also telling a story with minimal images and words, a skill that serves any writer well.
The most successful cartoons take only a second to land a laugh. Two students, talking before a concert performance: “Wake me up in time to clap!”
A woman standing next to a pile of bodies after a fight: “Madame Chairman, the committee has reached a decision.”
In other cartoons she takes aim at the faculty: “Do you think teachers are necessary?” WAVES (Women Accepted for Voluntary Emergency Services) were also a favorite target; the Navy used the college as a training ground before World War II.
The writer Kelly Gerald points to similarities between O’Connor’s cartoons and her stories, such as the wallflower at a college dance who says, “Oh, well, I can always be a Ph.D.” Fast forward a few years and you have Hulga Hopewell, the young lady with a wooden leg and an advanced degree in “Good Country People.”
And the cartoons served another purpose, Gerald writes: “Placing her work in the student paper was a way for a shy girl at a new school to find an audience, one that would appreciate her uniqueness and her talents.”
The Writer
The most famous painting at Andalusia is a self-portrait. Fans of O’Connor know it well: The author, her hair cut short, stares blankly ahead. She is seated next to a pheasant cock and appears to have a halo—or is it merely the Georgia sun? Painted in 1953, while O’Connor was undergoing treatment for lupus, it offers a sharp contrast to her cartoons. There is no hint of a smile.
It is an odd choice for a 28-year-old artist—even odder that she wanted to use it as her official author photo. (Her publisher demurred.) “Nobody admires my painting much but me,” she remarked. “Of course this is not exactly the way I look, but it’s the way I feel.”
Much had changed since her days at the college paper. In December 1950, at the age of 25, she was diagnosed with lupus. After stints at Iowa and at an artists’ colony in Yaddo, N.Y., and a stretch in New York City, she was now back home, living with her mother alone on the family farm outside of town.
Not surprisingly, her art from that period is more contemplative. She is not painting to relay a point of view but to develop her eye. “I know a good many fiction writers who paint, not because they’re any good at painting, but because it helps their writing,” she wrote in Mystery and Manners. “It forces them to look at things.”
There are paintings of pheasant, quail, ducks and chickens. Surprisingly, there are no peacocks, the animal O’Connor is most identified with. (Her later paintings do not have an exact date assigned; they were composed sometime between 1951 and 1964.) She painted what she saw every day: cows, the horse barn, a hill in the distance. You can see why painting appealed to her. It parallels the work of a writer. How do you describe a scene? What detail do you focus on first? What is the exact shade of that bull? (From “Greenleaf”: “squirrel-colored.”)
After I visited the art exhibit at Andalusia, I rode in a golf cart up to the main house. I took a few pictures and walked inside, first through the kitchen, and then into the front rooms of the house. Her bedroom was on the right. On her desk, in the middle of the room, was a typewriter. I have used a computer for so long that I can’t imagine what it’s like to write on a typewriter. But this is one thing that occurs to me: When you buy paper and impress ink upon a page, it’s not unlike applying paint. You have to commit—to an image or a word. It doesn’t have to be perfect, but it helps if it’s close. And that takes practice.
O’Connor was always on the lookout for anything that would help her writing. So she read Henry James and Thomas Aquinas and Pierre Teilhard de Chardin. And she painted, at one point even taking lessons from the artist Frank Stanley Herring. It seems notable, given conversations regarding O’Connor’s controversial treatment of race, that two of the people O’Connor chose to paint were Black, an older woman and a young girl.
The older woman is wearing a green dress and sits in a rocking chair. The young girl is pictured in a blue dress and a white bow in her hair. Robert Donahoo, an O’Connor scholar, notes that both women are dressed “not for menial chores, but in prim clothes—Sunday best my mother would have called them.” They carry a certain dignity, especially the young girl, who looks straight at the viewer.
In her stories, when O’Connor describes a pair of glasses, it’s time to pay (closer) attention. A metaphor is afoot. I would suggest a similar approach to her painting. When the subject is staring at you, the choice is deliberate. So what does it mean?
In her self-portrait, the image demands contemplation, like an icon. Here is a young woman reckoning with her mortality, her cheeks swollen because of steroid treatments. By placing herself at the center of the canvas, she is taking ownership of her condition, and her worthiness before Christ. Not for nothing does it resemble the mosaics of Christ Pantocrator.
What if we looked at the young Black girl in the same way? By staring at you, she is inviting you to recognize her dignity. When I first saw it, I thought, again, of “A Good Man Is Hard to Find,” when the grandmother spots a young Black boy by the side of the road—“If I could paint, I’d paint that picture,” she says. But where the boy in the story feels like an object, the girl in the painting comes across as a person.
An icon should force you to contemplate the person in front of you, but also yourself. It should lead to an examination of conscience. This is what Flannery O’Connor set out to do in her fiction. At the end of “Revelation,” one of the last stories published before her death in 1964, Ruby Turpin sees a parade of souls marching up to heaven, with “white trash,” “black niggers in white robes” and “freaks and lunatics” leading the way. The last are, finally, first.
Can we look at the least among us and imagine a soul on the way to heaven? Can a “visionary light” settle in our eyes?
Again and again, in her writing and in her painting, Flannery O’Connor urged us, simply, to look.
This article appears in November 2025.
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