Bob Oller: All-In for Art

Bob Oller: All-In for Art

By Linda Landreth Phelps

Great passion often compels people to perform desperate acts. “I used to steal my older brother Jerry’s art supplies when we were kids,” Bob Oller confides. “We were pretty poor growing up in Florida, and there was no money for extras. Jerry had been designated the one with artistic talent in the family, so he got the colored pencils and paper I coveted.” Oller had it down to a sneaky science, as he recalls. “I’d memorize how the pencils were arranged and return them exactly as they were in the box, right down to the sharpness of the points. I’d tear paper out of the middle of the pad, then hide while I worked and never showed my drawings to anyone. For years I thought I was stealing successfully, until the day my brother told our parents to start buying me the art supplies. ‘Bobby’s a better artist,’ Jerry said.”

Although he was never again driven to theft, Oller had to be determined and persistent to get his Bachelor of Fine Arts from the University of Central Florida. “Every class I could choose, I took art of some kind,” he says. Pottery, sculpting, fiber art, graphic design, he consumed everything and loved it all. He entered into the commercial world as a creative designer and illustrator, working in publishing and on the cutting edge of visual interactive media, honing technological skills that allowed him eventually to be a successful independent businessman. 

But even as he steadily progressed in his business career and made the move to Williamsburg 45 years ago, Oller was still practicing fine arts, never losing his first love for crafting beautiful images. The last of three agencies he created was Oller Studios on Jamestown Road. “After 25 years in the commercial art business world and mostly loving it, I think I finally became confident and resilient enough to take the leap of faith I always dreamed of—of making my way in the world solely as a fine artist.” Fifteen years ago, Oller closed up shop and moved his studio to the backyard of his home on Greensprings Road. 

If you are a visiting friend, or ever taken an art lesson at his kitchen table or attended one of the regular open house gallery tours, you know that Bob Oller’s house, tucked away under enormous trees in a bamboo forest, is just another reflection of his artistic vision. Every wall and surface feature something he created with the help and input of his wife, Jean. “Jean is an amazing, exceptional chef and my best critic,” the artist says. Together they have designed and built custom furniture for the interior and added outdoor space that includes a koi pond, a treehouse and a tiki bar. Its serenity serves as a perfect backdrop to the bold and prolific art. They have successfully combined their talents and environment to present a customized immersive experience. “An Evening with the Chef and the Artist” (boboller.com), includes a five-course gourmet meal for a limited number of guests in their home, with fine wine, artful conversation, and a detailed tour of the gallery. “This idea is rather recent, but the feedback has been wonderful so far,” Oller shares. In order to make a living as a fine artist, diverse income streams are necessary. His large-scale work can be seen in museums, commercial spaces, and hospitals as well as galleries, online, and at art shows, where his eye-catching professional displays attract the public’s interest.

  His clientele includes people from all walks of life. From a New York playwright who purchased a large canvas for his loft, to a teenager who is saving up to buy his first small Oller original, almost everyone can find something they love, whether it is an original or an affordable print. “I still do some watercolors, but mainly I do acrylic paintings. I like to work fast and manhandle the paint, mixing on the canvas as I go, as you would work oils, but quicker drying. I’m also known for a newer medium, vector painting, which is an exciting digital art form. There are others who use vector, but I love to explore the limits of every form of art and push past them into a new dimension,” he says. “However, every medium has its own challenges, capabilities and limitations, so I won’t settle on just one.”

During the art show season, the Ollers travel all over the mid-Atlantic region to major shows, with their faithful Havanese companion, Traveler, happily perched between them. They both enjoy being outdoors and meeting new people while selling current pieces and picking up new commissions, which account for a third of his work. Plein Air painting is another passion, and he is in the process of putting together a new series of workshops and painting retreats in different areas ranging from the Northern Neck to the jungles of Costa Rica. 

“I’ve fallen in love with teaching,” Oller says. “It’s so satisfying to see a student make a breakthrough and to observe the light of understanding in their eyes. I find that teaching makes me a better artist, too. By focusing on my student and seeing who they are as an artist and helping them gain confidence and skill, everybody wins. Getting into their head makes me paint way beyond myself.”

Oller has been privileged to travel to many different places over the years. The artist has done workshops in Jamaica and Puerto Rico but has a particular affinity for Cuba. A man of deep Christian belief, he visited that country for years as part of a missionary team. His experiences there as both an artist and a missionary changed his life and deepened his faith, which has been expressed in a series of digital vector paintings, the Cuba series. “There are 14 of them right now and at least six more to come, and they all have stories attached.” Oller, a natural born storyteller, has in the recent past done limited in-person exhibitions featuring only the 14 Cuban prints which includes time for him to tell the full narrative behind each of the pieces. 

“The Bishop of the Methodist Church there asked my team to be part of a baptism to be held at a remote beach location in 2019. We were miles from anywhere, but 2,000 people showed up. My group walked out beyond the surf line, ready to begin, but you could see a huge storm moving our way. The sky darkened and the waves began to kick up. It wasn’t looking good for the baptism, but we started praying hard for people as they began coming out to join us.” Oller pauses here to gather his emotions. He can seldom tell this story without being overwhelmed with a flow of silent tears.

“A hole opened up in the darkening sky and three beams of intense light fell on us, and the waves settled,” he resumed. “The beams followed us and never left until we had finished baptizing 468 believers.”  All of them were so moved by the experience that they could not bring themselves to come ashore. They stayed on in the ocean, celebrating together, holding hands and forming a circle, until the light beams were swallowed up by the sky. 

Later, the bishop asked Oller in his broken English to capture that striking scene in a painting, which now hangs in his office in Havana. “That’s the kind of story that I, as an artist, am looking to tell. I want to take light, color, motion, as well as a story and be passionately moved by what I create and also move others, to inspire them to want to become a part of it. It’s what an artist should hope for. This kind of art is what we all should have hanging in our homes.” 

The passion and excitement of a true artist is timeless. In his 70th year of life, Bob Oller is still all-in for art. There are always new challenges ahead, boundaries to explore and surpass, new subjects to paint, and beautiful blessings to both extend and receive. 

“I’m eternally thankful,” Oller says, “for the chance to live my boyhood dream.”

Explore more of the artist’s work at his website, boboller.com. His home and studio are open by appointment

Local shows:

In the Middle, Urbanna, Virginia, June 2025

An Occasion for the Arts, Williamsburg, Virginia October 2025