In the article, the researcher made a comprehensive study the American photographer Jerry Uelsmann art as a kind of contemporary digital photo-surrealism “prehistory”. The author revealed connections of Jerry Uelsmann works with American modernist photography and historical surrealist photography. The researcher analyzed the structure of Jerry Uelsmann’s hybrid images in the context of the ideas of analytical psychology, and also outlined the themes and concepts proposed in the works of the photographer that would be relevant in contemporary digital photography. The study showed that Jerry Uelsmann art continued the traditions of American modernist photography and started a new, post-modernist period in the development of photographic art in the United States characterized by the use of photography as a tool of self-knowledge and philosophical expression. Jerry Uelsmann applied such important for the historical Surrealist photography conceptions as convulsive beauty, the principle of “encounter of images”, surreality. He used experimental techniques (negative print, solarization, photomontage) and aimed to demonstrate the limitless creative possibilities of photography as well as the Surrealists. Uelsmann appealed to archetypal images which provided his works by intellectual simplicity and external showiness that contributed to the popularity of his photomontages and their strong influence on the development of contemporary manipulative photography. Uelsmann set a kind of “standard” for photo-Surrealism of the late 20th–21st centuries: these are technically perfect photomontages that require a high level of professional skills and time expenditure. Many of Jerry Uelsmann’s motives and ideas found parallels in contemporary digital photography. Among their common features it’s possible to single out concentration on the inner world of the person, interest in archetypes and symbols, the desire to poeticize nature, and the introduction of elements of mass culture into hybrid images.