Painting of a tree by Robert L. Lewis

Recently we got the chance to meet some true living legends. We met two of the 26 original members of a group called the Florida Highwaymen. This group of 25 men and 1 woman, are now famous for doing paintings of the beauty of what they saw around them in Florida. When they first started painting, their work was done as inexpensively as possible, and they traveled up and down A1A and I-95 in Florida to sell it. In selling these paintings these artists found a way to make money that didn’t involve working in fields or for other’s in any way. They were able to provide for themselves and their families by doing something that they enjoyed.

The man who was the original original (as I kept calling him that day) was Alfred Hair. He learned under a prominent white artist by the name of A.E. “Bean” Backus. Mr. Hair learned to paint the landscapes that the Highwaymen became so famous for. (The picture above – painted by R.L. Lewis – is one of those common themes.) When he realized that he could make a living at it, he began to teach those around him to paint and sell as well.

To begin with, people didn’t recognize their art as anything special. Then, as more and more people wanted pictures in their houses of the beautiful Florida landscapes, The Highwaymen’s paintings became more and more coveted. Now some of the original paintings sell for over $5000 each.

We met a couple at the show that has been collecting Highwaymen art for years. They said they have over 80 different paintings in their house, from all of the 26 originals.

The original 26 Florida Highwaymen were accepted into the Florida Artists Hall of Fame in 2004.

Florida Highwaymen artist Robert Lewis and two other people

We met Mr. Robert L. Lewis, who told us stories about playing football, teaching 4th graders to finger paint, and about some of his other life adventures. We got the distinct pleasure of being able to watch him actually painting while we were there. I could have stood there all day watching him paint. His love for what he does was evident. I love to watch people’s process. Mr. Lewis made it look so effortless. His son was there and he told us that he practices what is known as “wet painting”. Those of you who are painters will know exactly what he meant. I didn’t until he explained it. Wet painting is when you essentially keep the canvas, or whatever you’re painting on, wet the entire time you’re painting. The good thing is that you can manipulate the paint a lot easier. The bad thing is that you generally have to do the entire painting at one time. Mr. Lewis’ son told us that he will sometimes stand for hours at a time to finish a painting.

Robert Lewis Florida Highwaymen painting
Florida Highwaymen artist Isaac Knight and two other people.

Another original that we had the honor of meeting was Mr. Isaac Knight. Most of the paintings that are done by The Highwaymen are brightly colored. Mr. Knight had a few paintings there that day that were done in black and white. It was beautiful to see the detail that he could capture in black and white.

I read before going to the show that most of The Highwaymen painted similar subjects, but that if you look, you’ll see the style differences between them. Mr. Knight’s black and white paintings were a perfect example of this.

Artist Kelvin Hair and two other people

We were also able to meet Mr. Kelvin Hair. Kelvin is the son of the original original, Alfred Hair. His father passed away when he was 5 years old, but Kelvin still picked up his father’s love for painting. He learned the Highwaymen style under some of the other originals, and then also began painting his own subjects. His paintings were so beautiful. They all seemed to have something about them that stood out because of the technique and the colors that he used. The longer I stood and looked at his paintings, the more detail I saw.

If you would like to read the full story of the Highwaymen, start here.

The story of The Florida Highwaymen has always inspired me. When there wasn’t a way for them to do what they wanted to do, to live their dream, they created a way. Their circumstances were less than ideal (to say the very least), but they still made the effort to better themselves and their lives. A lot of people use the fact that they had a hard upbringing as an excuse to stay where they aren’t happy. What that really means is, they aren’t willing to do the work that it takes to make their dream happen. The inner work, or the outer work.

It was a slow road for most of the Highwaymen. Success and money wasn’t an overnight thing. In fact, most of them made enough to live their daily lives and not anything more. When we think of living the life of our dreams we often think of having the money to do whatever we want to do and never having to work again. More realistically, living our dreams means doing what we love to do, working for ourselves, and having the freedom to do what we want to do, when we want to do it. It doesn’t mean that we never have to work again. It doesn’t mean that we have anything and everything that we want with the snap of our fingers. It simply means that we are doing what we love instead of doing what we think we have to. It means that we can take a trip, or take the day, without having to ask someone for time off. It means choosing how we spend our time instead of being told how we must spend our time.

The Florida Highwaymen create beautiful art. Some of it I could stand and look at for awhile and keep seeing more and more details. It’s the story behind that art that truly inspires me. I hope it will inspire others to seek out their best lives as well. To help them see that, just because they don’t see a way in the world to use their unique talents, doesn’t mean it’s not possible. If you can’t see a way, then create your own path. It may take a little longer, it won’t always be easy, but it will be worth it.