harry underwood

Harry Underwood, a self-taught painter in Tennessee, creates scenes of everyday people on vacation or enjoying themselves in his nostalgic, outsider-style works.

“My paintings look like postcards from a better world” said the soft-spoken artist. “But if you read them, you find more depth than that.

“I think that people dream of wealth and identify leisure with wealth. I’m trying to say that it’s not true. All that you will ever need is your life.”

Artist: Born in Coral Gables FL, Underwood grew up in nearby Homestead and Miami.
After being expelled from school in the 11th grade, he went to work but returned two years later to complete his high school credits in night school.

After high school, Underwood cleaned pools, bussed tables, worked in construction and as a house painter.

In the beginning: Underwood always drew pictures and thought about self-expression.
In 1997, he began to think about ways he could turn his drawings into paintings. He used photo copiers, sketches, picture books and magazines. He also tried different products: charcoal, pastels, crayons, colored pencils, water colors and oil paint.

“I contemplated subjects that would associate well with my background,” said Underwood. “I wanted to make art from my personality and family background.”

Studio: Underwood has worked in his home studio in Springfield, TN, for 25 years. He paints in a small, crowded room that is 12 x 14 feet, thankfully with a window. In an outdoor shed, Underwood cuts wood for his picture frames, which he builds in an area of the basement.

Art & materials: Paintings, using pencils for hand-written text, latex house paint, wood stains, acrylic varnish and wood panels, usually birch or maple. ($1,800 to $16,000. Most commonly, 26 x 26 inch is $1,800).

Influenced by his early Florida surroundings, Underwood’s paintings often feature motel pools, dancing couples, women in bathing suits and palm trees — showing people on vacation or enjoying activities outside of jobs.

For his text, Underwood has often quoted the Bible, but other writings are his own.

“I use pocket notebooks I carry around,” said Underwood. “I usually will write something fresh for a painting that can tie a picture with that moment in my life.”

“It’s similar to magazine advertising when I combine text and image,” he added. “If I put three words written large above the picture it becomes a slogan.”

Are you an outsider artist: “Yes, I think that I am,” said Underwood. “Although I also agree with people that say all artists are outsiders.”

Favorite tools: Table saw, X-Acto knife, pink copy paper and various kinds of pocket notebooks.

Influences/inspirations:

Miami Beach and the Everglades.
Isolation, said the self-described loner.
His memories.
The 1969 movie, “The Bed Sitting Room.”
Classic books, including “The Sirens of Titan,” by Kurt Vonnegut Jr. that he read as a young adult. And most recently, “Maggie: A Girl of the Streets” by Stephen Crane.
Howard Finster. “I appreciate Finster’s use of ordinary materials some of which I adopted, like wood and house paint,” said Underwood.
Other artists, including Gauguin, Toulouse Lautrec and Juan Miro. “My knowledge of art came from a very old art book called “The History of Art” published in the 1960s,” said Underwood.
“Adulthood. Because it’s when life really began for me,” he said.

Recent project: A 38 x 74 inch painting titled: Do not envy the violent or choose their ways. “The passage is from the Bible,” said Underwood. “I am against violence.”

What’s next: Outsider Art Fair in NYC, Booth 11. March 19-22, 2026. Underwood will be there in person on Sat., March 21, from 11 am to 5 pm.

Where to buy: