Winningham has produced three documentary films, including The Pleasures of His Stately Dome, a study of the Houston Astrodome as a folk theater, winner of the Documentary prize at the Edinburgh Film Festival in 1976. He has written and photographed numerous magazine articles, most often for Esquire, Texas Monthly, and Travel & Leisure. In addition, he is the Company Photographer for the Houston Ballet, a position he has held since 1977.

His work is also included in many major anthologies of photographs, such as 20th Century Photographs from the Museum of Modern Art (1983), Courthouse (1978), Faces: A History of the Portrait in Photography (1977), and Masters of the Camera (1976).

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