Kelvin Hair and the Highwaymen of Florida

Second generation Florida Highwaymen artist Kelvin Hair joined me on my “Welcome to Florida” podcast in February of 2021. Kelvin is the son of Alfred Hair, one of the original, legendary, Highwaymen of Florida painters. Alfred died at just 29-years-of age when Kelvin was only 5. Fellow Highwaymen would later adopt Kelvin into their ranks when he was ready to pick up the profession, especially Johnny Daniels.

Kelvin shared numerous stories on the podcast remembering time spent with the Highwaymen of Florida, Al Black in particular.

“(Al Black) would tell you in a minute, ‘I may not be the best artist in the world, but I’m the best salesman that was ever born.’ He taught me how to sell; he really did,” Hair remembers.

Hair saw this up close on his first trip out on the road selling paintings with Al Black after Black was released from prison in the early 2000s.

“Quite naturally I wanted to experience this, but I’m thinking in my mind, because by this time, the artists have been inducted into the (Florida) Artist Hall of Fame, it’s not $25 anymore (for a painting), you know, a 16×20 (inch painting) I’m selling at that time for like $1200,” Hair began. “I was like, ‘we’re not going to get $1,200 a painting out of the trunk of our car anywhere, but I wanted to go on the road with him. And I’m just meeting him. He told me to meet him at his house, so I met him at his house and I got probably 20 paintings with me; I start thinking like, ‘man, we’re not gonna’ sell nothin’ and ‘I’m not gonna’ carry all these paintings with me.’”

To lighten his load, Hair only took two paintings along.

It was a decision he would regret.

“He got in his car and we jumped on the road and we rode for about an hour and 15 minutes across the state. We stopped in is one spot, by this time it must have been nine o’clock; I sold both my paintings for $1000 and I was going around with him watching him watching sell all his paintings the rest of the day,” Hair recalls vividly. “If I would have brought the rest of my paintings, we would have sold them.”

Now a believer, Hair recalled another Highwaymen of Florida “on the road” story. In need of a car after breaking up with a girlfriend, Kelvin Hair called Al Black to meet up and sell some paintings.

“We struck out the next morning on the road (and) I made 16-grand out the trunk of the car. I tell you, Al is the best salesman I’ve ever seen,” Hair said. “His memory is impeccable. I was driving one day, we were on the road again, now, Al and I have been on the road hundreds of times. I’m driving and we’re over around below Clewiston (Florida) somewhere and Al’s like, ‘take a right here.’ ‘Make a left here.’ ‘Turn here,’ and we’re off the main road. Then we come up on this privately owned hardware store.”

The story gets even better from here.

“We went in there and the guy remembered Al. Al was looking for his dad; his dad has passed, left the hardware store to the son and the son was like, “I remember you, I was like 15-16 when you used to come around here selling paintings to my dad,” Hair remembers. “The guy’s acting like he doesn’t have much money, he’s not sure, but the more we start talking, the more he realized Al was for real and who he was and so now that he gained trust in us, he took us in the office – this is true story – Al and I sold him some pictures, I think I might have made maybe four or five grand, Al made probably around the same, four or five grand, but the guy was faking like he had no money. But after he trusted us, he took us in the office, he reached into the safe, and he had a stack of money – when he pulled the money out for us, it  did not even touch the stack. That’s how much money he had in the safe. When Al saw that, I don’t know what happened, but Al took this guy off and started talking to this guy and ended up selling him three more paintings for more than what he sold him the past six for. I’m like, ‘how did you do that?’ If you listen to Al, you will buy a painting. Period.”

During the interview, Kelvin mentions a book titled, “The Highwaymen Murals: Al Black’s Concrete Dreams.” The book centers on the murals Al Black painted while incarcerated in Florida after being found guilty of embezzlement. You can find the book online here.

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