Operating a newspaper means you get a lot of letters in the mail. By small-town standards, The East Hampton Star receives a ton — most of them by email these days, endless missives allowing the editor and publisher to know exactly where its readers stand on any given topic, from parking-ticket protests to muskrats in Town Pond.
Meet Anita Fagan: former pharmacy clerk, James Dean fan, and outsider artist.
For about 30 years, this Southold resident has been writing to The Star, often sending in painted portraits or landscape scenes on canvas board or paper, sometimes with a little poem or message on the back, always in a manila envelope bearing her cursive penmanship. The bottom part of her lower-case ‘p’ takes a big scoop out of the page as the capitals in her name trail off auspiciously toward the right margin.
Anita Fagan paints celebrities and in certain circles out here is something of a celebrity herself.
The details of Fagan’s life, as told to a reporter, are a bit blurry. She’s either 80 or 81 years old, she said, but she definitely has three children. She wears her silver hair like a 1950s glamour queen.
She said she was a professional tennis player at one point in time, with “a terrific backhand, a terrific overhead serve.” She also said she worked at the pharmacy that her father owned in Greenport, and that she left when she was 20 years old to start her family.
As the distinctive whistle of the Andy Griffith Show’s opening theme played in the background, Fagan sat for an interview in late May. She said the television keeps her company. “Three husbands died. I’m alone, so I leave the TV on.”

Ever since a bout with pneumonia a few years ago, she has used an oxygen tank, but she dislikes wearing her glasses because they fog up constantly.
Judging by the vast number of portraits that fill her rooms, she spends a lot of time creating her artwork. Between art and television, she keeps her routine simple, eating things like pierogies, hot dogs, or frozen chicken legs for supper, for example. “I don’t have my children with me, so I don’t really make big meals anymore.”
She paints for six or seven hours a day using supplies her brother takes to her occasionally. Fagan has been making art her whole life, she said, except for when her kids were little. “I was an artist the whole time, but when you have children, you don’t do it as
steady. You have to take care of your children. Now they’re all grown up and I can draw every day.”
The day of her interview, she was working on a painting of a cardinal. “Art is something to do. The artwork keeps me happier than you’d believe. I’ll be feeling down in the dumps and I’ll start painting and feel heavenly. It puts me in another world.” She also recently made one of four hyacinths in a vase, in a blue frame, with a window nearby. “That one really impresses a lot of people,” Fagan said.
The bulk of her art, however, is portraits of famous people, including Robert De Niro (“He’s from East Hampton, you know”), Humphrey Bogart (“I’m related to Bogart, you know”), Cary Grant, Queen Elizabeth, Princess Diana, and Ronald Reagan (“He used to take me to rodeos”). But James Dean is her favorite subject to paint. “I’m from the James Dean Cult of 19, like, 55,” Fagan said. “When he got killed in a car accident, I couldn’t get over it. He was just so different from Elvis Presley. I liked James Dean better. When I was going to school, I had his face and hair. I combed my hair the way he combed his hair.”
She has sent more than one James Dean to her favorite newspaper. Around Thanksgiving one year, a painting-letter arrived at the Star office on Main Street portraying James Dean “if he got older.”
“To the Star,” she wrote on the back. “A paper who gave me life.”
“I wrote to many papers,” she explained, “and I would get letters back saying, ‘I’m sorry, we cannot use your letter.’ I liked The East Hampton Star because it was a country paper, and they took my letters. They took everything that I wrote.” (The Star has long maintained a policy of printing all letters to the editor, as long as they are not libelous or copies of letters sent elsewhere.)
Her epistolary relationship with The Star started about 30 years ago with a couple of editorial cartoons. “I sent in a drawing of me on a bicycle and they put it in the newspaper. Underneath it was a little poem, “Wartime Stories.” Then I sent one of George Bush eating a pizza, and he’s on the phone and says, ‘Gorbachev, send me some pepperoni.’ And it was a joke, but it was on the third page.”
The walls of every room in her house are covered with her paintings, all in frames she painted in Caribbean Blue, according to the name on the tube of paint. “I find the frames sometimes make the picture,” Fagan said.
The colors keep her company. She speaks of them like friends with personalities: Princess Purple, Paradise Pink, Candy Apple Red, Clover Field. “I like working with colors, making colors different, and making new colors. I want to make colors that nobody’s
seen.”
She goes through paintbrushes the way some people go through boxes of coffee filters, so, sometimes, she skips them altogether. “Ever hear of fingerpainting? You want a better picture, finger painting is better, but you have to use gloves otherwise you get paint all over your fingers.”
In one particularly vulnerable moment, Fagan wondered whether anyone’s seeing her paintings.
Yes, a writer reassured her, people are seeing them. They’re displayed all over the Star office — in the lobby, in the kitchen, in the newsroom, in the editor’s office. People are seeing her paintings. And they are fans.
