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1800 Denn John Lane Kissimmee, Florida #FloridaHighwaymenOsceolaGallery
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Gallery Exhibit

Mary Ann Carroll: First Lady of the Highwaymen

Event Manager and Gallery Director: Professor Kathryn Cairns,

Location: Osceola Campus, Osceola Gallery, Building A

Date/Times: September 10 through October 26, 9am-4pm (Monday-Thursday)


Speaker Series Event and Reception

The Highwaymen Florida’s Landscape Painters: Gary Monroe

Location: Osceola Campus, Building 1 Rm 101, Auditorium

Date/Time: October 2nd at 11:30am


In the early 1960s, with boundless energy and enthusiasm for making art and money, the African American landscape painters, later known as the Highwaymen, were well on their way to inundating our state’s east coast with their interpretations of Florida as Paradise. They worked quietly during those days of segregation, “like shade-tree mechanics,” recalls Mary Ann Carroll, who, as a core member of this collective, had contributed her supreme color sensibility to the group’s aesthetic.

Because they could make and sell more paintings by eschewing the classical formulas, speed determined their style and their style resonated with Floridians. These marginalized artists, first admired because of their going beyond the social expectations of their time, visually documented a bygone Florida while profoundly changing nostalgic landscape art techniques.

Once Highwaymen paintings graced their walls, Floridians could put themselves back into the dreamy tropics of the post-war boom. Content with being unrecognized in those early days, these painters capitalized on those romantic versions of Old Florida to earn them a lot of money. Fortunately for all future Highwaymen fanciers, making “an honest dollar for an honest day’s work,” as Mary Ann puts it, was primary in their motivation; thoughts of becoming revered artists never inspired them. Surely their visceral reaction to Florida’s landscape would have been lost had they been self-conscious, painting with others’ artistic sensibilities.

Business remained brisk for more than two decades, into the early 1980s, when Highwaymen paintings lost favor as modern Florida emerged.  New symbols replaced the old as the state was on its way to homogenization.  Many people now were more attracted to the man-made hues of amusement parks than the ones found in a Florida sunset.  “People just stopped buying our paintings,” said Willie Reagan.  Nevertheless, existing Highwaymen art is finding new life in the hands of collectors as quickly as those old paintings make their way back into circulation.  These paintings are forever unique; they tap into the awareness of our surrounding area and shared culture as Floridians.   

Event Details

  • Jasalyn Sancio
  • Julianna Walker

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