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With no initial intention of doing so, the group of young men (and one woman) were creating an American success story unlike any other. And behind the scenes, a beautiful dichotomy began to form between the two founders of the group. Harold, under the admiring influence of Backus, sought to preserve the techniques he learned. He was interested in being the best artist he could be. Alfred however, aspiring to be a millionaire by his 35th birthday, had only one interest: being the richest artist he could be.

At the time, Backus was primarily painting on commission, and a typical Backus painting would cost a few hundred dollars (a decent amount of money in the late 1950s). Hair’s business savvy provided a solution: rather than model Backus spending six hours on a single painting that would sell for $300.00, he knew he could paint ten paintings in that time and sell those for $30 each. Acknowledging that they would be lower quality, his target audience was no longer the rich and wealthy, but the average American.

Sam Newton Highwaymen Painting

SAM NEWTON, c. 1990s

Some artists painted faster than others, with Hair being the fastest. It's said that he could paint up to 40 paintings in a day. Newton often stressed the importance and value in creating higher quality artwork, while Hair was primarily concerned with creating a higher quantity of artwork (and in turn, more revenue).

Both possessing incredible skill and drive, Hair and Newton's artistic decisions created the yin-yang of the movement. One ushered in a desire to create great art, the other to create great wealth. Both earned immense respect from the other artists as well as the community. Drawn to the lifestyle and success, the group forming around the two consisting of neighbors, family, and friends, had now turned into a entrepreneurial enterprise like no other. Not only were these young men and women able to create a living for themselves in an unimaginable way, but they were getting good. And as their skills increased, so did their sales.

Al Black Highwayman Painting


Sam Newton Painting
James Gibson Painting
SAM NEWTON c. 1970s
Willie Daniels Painting
Rodney Demps Painting


Part of what makes Florida Highwaymen artwork so extraordinary is the tangible legacy included with each painting they produced. The legacy of the Florida Highwaymen is not just a story, but a physical history you can see and feel through their artwork. They captured the beauty of Old Florida in each of their paintings, but every painting is still unique. Scenes were replicated, and techniques imitated, but each artist had their own distinct style, color palette, and skill that set them apart from each other.

Here we have four paintings, all by the original members of the group. As you can see, each painting includes similar elements: a bent palm, a poinciana tree, colorful and imaginative. However, each piece is also inherently unique due to the artists distinct abilities and styles. This is part of what makes collecting Highwaymen artwork so fun, addicting, and fascinating. No two pieces are ever the exact same.

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