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This article aims to consider the concept of personality proposed by the prominent exponent of Russian neo-Kantianism Sergey Hessen and its philosophical and legal content. The frame of reference used to achieve this aim is determined by the personality-culture-the general will-the state coordinates. The author compares Hessen’s ideas with Bogdan Kistyakovsky’s legal concept. Hessen distinguished between several layers of meaning in the notion of culture — civilizedness, level of education, and civic virtue. He stressed that the personality and culture existed in a dialectical relationship. Hessen emphasised the primacy of personal freedom and the need to distinguish between freedom and power of choice. Acts of choice are random and unpredictable — they do not have a solid foundation, whereas acts of freedom are a prerequisite for creativity — an integral characteristic of personality. The creative essence of personality suggests individuality and uniqueness of each person. Personality has a historical dimension. In analysing the problem of the relationship between a person and society, Hessen considered Rousseau’s concept of general will. Hessen proposed a dynamic understanding of general will as a continuous process of establishing and re-establishing that involves the general population. Hessen counterposed law against the notions of nature and morality and interpreted law as an insufficient but necessary prerequisite for harmonizing relations in a society. Hessen developed an original understanding of the ideal of state organisation — a democratic state that incorporates the principles of liberalism and socialism.