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Roy A. McLendon Sr. was born in Pelham, Georgia in 1932, and he is the oldest living member of the group. He moved to South Florida at the age of fifteen and eventually settled in Gifford. He was in his 20's and working in the groves when he met his new neighbor, Harold Newton.

McLendon would often watch Harold paint in his yard across from him, and after a short while he picked up painting himself. He started out very purposeful, and has remained so throughout his entire career. He did his own selling on the road, and would only go out on a sales trip after painting a handful of good paintings. He rarely sold anything rushed, which is likely why there are very few poorly done paintings done by Mclendon.

McLendon (being one of the earliest members) is credited with helping some of the younger artists get their start. He was close friends with many throughout the group including Alfred Hair and James Gibson, but was closest with Harold Newton, Livingston Roberts, and Mary Ann Carroll.


After many years of devotion to his career, Roy McLendon Sr. passed in March of 2024. He will forever remember the kindness of such an incredible member of the community, as well as talents as an original Florida Highwaymen Artist.

Biographies are adapted from those on, one of the earliest informative websites on the Florida Highwaymen. Since the site is no longer active, we have provided them here.

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