After 1991, the proclaimed Second Republic of Estonia restores individual freedoms, which leads to the problems of individualism, personal borders, transgressive behavior, identity, equality and corporeality in Estonian art after the 1990s. In this article, the author will examine the works of key Estonian contemporary artists who address the problems of identity crisis and “split personality”, which are so characteristic of modern Estonia, where issues of cultural memory, national identity and disciplinary authority are acutely relevant. Marge Monko and Liina Siib analyze the construct of “femininity” and various female cliché images through the sociocultural phenomenon of hysteria. As a result, the author comes to the conclusion that in the context of the identity crisis that reigns in modern Estonian society due to historical and geographical circumstances, artistic representations of a split, “hysterical” personality, embodying established social and cultural patterns that affect individuals, become especially relevant. Through both self-analysis and analysis of the collective unconscious, the artists seek to reveal the reasons for the oppression of “deviant” behavior, as well as the influence of “foreign” culture on Estonia.