The article researches the topic of “artistic distrust” as a possible rebel path of the rebellious artists from the mainstream to the underground existence. The artist’s existence of reality on the principle of doubt about any norms (the model of “anthropology of distrust”) has a long historical longevity. Through the analysis of both high-quality works of art and safe normative art in different periods we observe various examples that may show this point of view. In medieval art we notice the precedent of “disobedience” and non-compliance with the norms of the official church in decorations of the temples and overcoming of anonymity. Thus the artist Anton Pilgram resorted to self-affirmation, as long as the master signed his own work in the spotlight and made a self-portrait on it.From the Renaissance, the idea of individual search, experiment, that is, disobedience and doubt in traditions, has been working in the minds of Europeans. The latest philosophical thought of the beginning of the “anthropology of distrust” sees its origins in the worldview models of the Renaissance. Leonardo da Vinci, with his curiosity and the genius of exploration, has remained an iconic figure to this day and an obvious symbol of total doubt and distrust of all that is established. With the ideal of a beautiful, flawless man, philosophy and art parted with difficulty, in the dramatic realization that it was time to present the unattractive, the ugly, the unfinished, and the negative as artistic qualities in the works of the New Age. “Anthropology of distrust,” doubting the inviolability of existing (at different times) norms manifests itself dualistically. In the works of great masters the denial of norms thatexisted in the art of a particular era had a progressive, positive meaning, because it opened up new levels of worldview to culture. In global art practice, the vast majorities of artists were and are conformists. Conformism in art supports tradition, holds the level of skill, but has no pretensions to open new horizons in the artistic reflection of the world. The situation is quite different when the artist questions any stability in art, or totally denies them. This is not a riot for the sake of a riot, but a feeling of something missing that the artist himself is not yet able to explain. According to the promising thinking of the bright philosophers of the 17th–20th centuries, self-distrust, doubts about the perfection of one’s own achievements, and a look into the non-existent are productive for culture. These impulses of the psyche proved to be fundamental and indisputable in the mentality and culture of modern times. The most radical were the programs of Dadaism and Futurism. In a person of the pre-modern era, the deviation from the norm caused stupor. Now the procedural features of the “anthropology of distrust,” the feeling of one’s own deficiency activate the artist’s creative thought and encourage a reckless search, sometimes even complete self-denial. At all times, until today, the bravest in their own rebellion against existing norms (both artistic and social) often fall on the margins of life and the artistic process, or even underground. Such artists are not understood or supported by the general public, and even worse, they are treated with suspicion and sometimes hostility. In the early 1990s, when the young generation of Ukrainian artists opposed the remnants of the Soviet mentality in both art and social life, the “anthropology of distrust” had a life-giving meaning. The mobilizing philosophy of “distrust” regarding the normative nature of socialist realism led to the formation of Ukrainian “contemporary art” which later turned into neo-conformism.