Jennings attended school through 5th grade. His mother later educated him at home. He worked at the family tobacco farm until 1950, then night watchman at a drive-in theatre owned by his step-father. Watching adult movies made his nerves “go bust” and he returned to take care of his mother until she died in 1974.
Jennings began his art making after his mother died. He began to make whirligigs and signs and turned the yard into an environment. He had a series of old busses and loved in one of them: filling the others with his wood carvings. Although he had a sister living in town who was supportive of him and handled his financial affairs, he preferred living alone with his busses and cats. Jennings created elaborate works, expressing his personal and religious views. He used scrap wood, metal, plastic and what was around. He used Day Glo outside paint and enamel. His work often was enriched with multiple tight dots. His work ranged from 7” to 7 ‘.
Sadly, he committed suicide in 1999. He was a much loved fragile man.