Checefsky received his BS from Kutztown University of Pennsylvania and his MFA from Cranbrook Academy of Art. He is the writer and director of the short film Pharmacy, and he has had solo exhibitions Wexner Center for the Arts, Columbus, OH; Museum of Contemporary Art, Cleveland, Ohio; Institute of Contemporary Art, Sofia, Bulgaria; Galerie Tolgyfa, Budapest; Academie de Art, Bucahrest, Romania, and other venues. His films and photographs are held in many permanent collections, including the Museum of Modern Art, New York; Whitney Museum of American Art, New York; Minneapolis Institute of Art; Brooklyn Museum; Cleveland Art Museum; Fotomuseum Winterthur, Switzerland; and Institute of Contemporary Art, Bulgaria.