Fort Lauderdale lawyer Scott Schlesinger came to be
one of the largest collectors of Highwaymen art began
with boyhood memories of his father’s Hollywood
Sheldon Schlesinger’s 1960s walls had been decorated
with cheap but beguiling oils of Florida landscapes
by some of the 26 mostly self-taught African-American
artists from Fort Pierce who sold art from the trunks
of their cars along the state’s coastal roads.
Today, these artists are known as the Highwaymen.
The images evoked by those paintings – the deep
hued brilliance of Poinciana trees, wind –swept
palms bent against the foamy sea, backwoods roads at
dusk – would lie dormant within Schlesinger’s
memory for more than two decades before they reemerged.
“I was in Lakeland for an appellate hearing in
the courthouse,” says Schlesinger, a suspender-sporting,
third-generation Floridian. “I was drawn to the
art, to these beautiful, postcard pictures of Florida.”
Schlesinger, 49, already a passionate collector of Florida
landscapes, many of which grace the walls of his two-story
Key West-style office, began chasing and promoting the
works of the Highwaymen. He invested in their newfound
glory because he says he believed in the artists and
the making-do story that inspired them.
Schlesinger discovered the power of this regional art
movement – now the subject of websites, several
movie scripts, festivals, a PBS documentary, a heritage
trail and half-dozen books, including Catherine Enns’
The Journey of the Highwaymen (Abrems, $40), published
in April. Enns, who grew up in Fort Pierce, includes
images of several of the paintings in Schlesinger’s
collection. More are on display through June 30 at eh
Spady Cultural Heritage Museum in Delray Beach.
“Scott is a patron of the arts. He is generally
interested in the Highwaymen art and Florida art in
general,” says photographer Gary Monroe, author
of three books about the Highwaymen. “Growing
up here, he has an authentic connection to these paintings.”
Almost since that moment in the courthouse, Schlesinger
has pursued the Highwaymen’s story, an enduring
narrative that springs from the intersection of art,
commerce, race and Florida history.
During the fog of segregation in the 1950s, landscape
artist A.E. Backus, a middle-aged white man, opened
his Fort Pierce studio to black students, oblivious
to or because of racially divisive social norms. He
mentored Harold Newton and taught Alfred Hair, the best
known of the Highwaymen. Hair taught others. From these
improbable roots developed an industrious, bohemian
cooperative of 25 men and one women. The group eventually
produced up to 200,000 paintings – each artist
driven by the possibilities of a quick and decent dollar
without having to spend hard hours of labor in the citrus
The landscapes of tropical and rural Florida were often
assembled factory style, painted on Upson board or Masonite,
framed with crown molding and sold for $10 to $45. For
these artists, the paintings were a creative means to
an end. For their customers, the art was an affordable
and nostalgic, if unconventional, way to cover the paneled
walls of suburban Florida.
“Initially, I was just looking for a way to make
an honest living,” says James Gibson, 71, who
still makes his living as a painter in Fort Pierce and
has landscape on display in the White House. “I
Started out making frames for Alfred Hair. Then I started
painting, more as a friendly competition with Hair.
We painted as fast as possible. Others could paint better,
but I tried to study Me. Backus. I finally slowed down
like he told me and really began to work with the colors.”
Almost as quickly as the art became vogue, its popularity
waned, forgotten in attics or sold at garage sales and
flea marketing. Some Highwaymen continued to paint in
obscurity. Some stopped painting altogether. Al Black,
the group’s top salesman, went to prison, where
he ended up painting murals. Hair, the leader whose
pace and sweeping techniques came to define the style,
was murdered in a bar at 29. Schlesinger would later
scour Fort Pierce police records to identify his shooter
for a documentary.
The artists might have remained a quirky, dim chapter
in Florida’s history without the efforts of Jim
Fitch and Gary Monroe, who embraced the bona fide genre
that captured an idealized, if not quite mythical, vision
of Florida’s past.
Fitch, an art collector and museum curator, published
articles in art and antiques magazines and in 1995 coined
the Highwaymen name, giving the artists an identity,
even though some shunned the term for its possible negative
connotations. Monroe’s first book, the definitive
The Highwaymen: Florida’s African-American Landscape
Painters, published in 2001, traced the art from neighborhood
oddity to collectible, fueling its renaissance.
Almost a decade later, Highwaymen art continues to be
celebrated as American folk art, rather than as kitschy
souvenirs of old Florida. The artists (19 are living)
were inducted into the Florida Artists Hall of Fame
“Artistically, the Highwaymen are important because
they created the work of the people. They created folk
art, “says Robert Hall, a visual-arts specialist
at the Smithsonian’s Anacostia Community Museum
in Washington D.C. “You are talking about people
with very little formal training driven to document
history and the topography of the land.”
Schlesinger’s art epiphany unfolded about 1998,
several years into the revival, as Florida rediscovered
its mid century roots, and the prices of the art began
to soar (and original Highwaymen painting now fetches
up to $30,000.)
Artist R.A. “Roy” McLendon escorted Schlesinger
back in time.
“After I saw the art in the courthouse, I had
a couple of dealers come to my office to present paintings
for me to buy. One of them was a McLendon deep sunset
in the back country. It was black and orange and primitive
in nature,” Schlesinger says, sitting in his office
filled with works by Canadian-American impressionist
Ernest Lawson alongside Highwaymen art. “And it
hit me, this was like the pictures I had seen as a kid
growing up. All of a sudden, this buried childhood memory
Schlesinger is midway through the story when his father
strolls into the room.
Are we talking about Highwaymen art? I bought those
paintings still wet from the trucks of the guy’s
cars,” Sheldon says. “Musta paid $35 bucks
each. I really liked the art. But like all things, they
Until now, Scott Schlesinger purchased that McLendon
picture for about $300, moved by what the oil postcard
symbolized. For him, it captured Florida’s most
precious native scenes, intrinsically told stories and
somehow protected memories.
“I was looking for art showing the landscapes
before everything changed. I still remember the sugar
sand and the scrub, the oak trees and burrowing owls
and indigos snakes and red-cockaded woodpeckers, “
he says, almost wistfully. If you are old enough to
remember that Florida, then you miss it.”
Schlesinger was born in Miami and grew up in Hollywood.
He spent summers at his dad’s hip, fishing at
Hollywood beach and playing along its dunes. He lived
in a house on Fillmore Street in a new subdivision in
which some of the lots were still carpeted in scrub,
pine and palmetto.
He went to Brown University, then followed his father’s
path, becoming a civil trial lawyer. He now lives in
North Miami with his wife and three children.
The McLendon piece was the first of a collection that
has blossomed into at least 100 paintings. Schlesinger
turned to the internet, now a brimming marketplace for
Highwaymen art. He bought a Sam Newton online for $800.
The owner had paid about $5 at a flea market.
Something about the pictures intrigued me, and I wanted
to know more. I just felt like I had a responsibility
to really learn the art, the techniques, the colors
the compositions,” he says. “And the stories
behind the art.”
Eventually, he began narrowing his choices to rare paintings
featuring people and Highwaymen “trios”:
Backus landscapes and their interpretations by Hair
One of this most prized pieces is believed to be a self-portrait
of Newton. The image, unfolding in stormy blues and
greens and a pop of red and dating back to the 1950s
and 1960s, shows Newton sitting on his porch steps,
head arched back, guzzling a bottle of something good.
His mama, hands on her hips, glares disapprovingly.
Schlesinger, who already owned more than two dozen Newton
paintings, waited for more than two years for the owner
to sell before finally striking a deal a few weeks before
Christmas in the parking lot of a prison in West Palm
Beach. He also helped underwrite two of Monroe’s
books, a documentary that eventually ran on PBS and
an exhibit at the Museum of Art in Fort Lauderdale.
Highwaymen Newton & Hair: The American Dream in
the Sunshine State, which opened in 2006, explored the
work and motivations of the two most well-known artists.
Schlesinger says he has pulled out several other projects
because he believed they were more deal-driven marketing
efforts to sell the art rather than those that add scholastic
or cultural value.
Now, he is on board to invest in a movie portraying
the lives of Hair and Newton, if the project gets off
“The art resonates because it is Americana. I
want people to have the opportunity to absorb the art,
which provokes discussion and consideration, “he
says. “Yes, absolutely you can collect art. But
you should share it.”
Schlesinger holds Wash Day, a painting by Alfred
Hair, ouside his Fort Lauderdale Office.
Gibson, 65, poses with the "Orange Avenue Extension,"
left, and "Tallahassee Swamp," right, at his
home in Fort Pierce in 2003. Gibson, is one of 26 artists,
called "Highwaymen" who painted Florida landscapes
for spare change in the 1950's, traveling up and down
Interstate 95 to sell their paintings because no gallery
would give space to black artists. But in the last few
years, their paintings have gained new respect and often
receive several thousand dollars.