The purpose of the article is a culturological and philosophical understanding of the borderline phenomena of modern culture that arise on the border of different traditions, life strategies, cultural and artistic spheres. The relevance of the study is associated with the methodological and existential need to comprehend some phenomena on the border in the conditions of postmodern culture (intercultural inter-borrowing, ideological crisis, methodological pluralism, consumer society, ethical and aesthetic disorientation, scientism and non-scientific practice of knowledge and experience, etc.), which can be extrapolated to other similar trends, and practically-existential significance associated with the real need to search for and create a compromise and creative platform for the "dialogue of cultures", cultivating and feeling the unity of man and the world, man and man, implementing balanced and holistic strategies of life in society and an individual. The nature of jazz as a cultural phenomenon, which embodies the freedom of musical thinking, spontaneous improvisation, imaginative dynamics, a special receptive environment and an atmosphere of openness, changeability, acceptance, capable of generating new (other) musical and cultural phenomena, is analyzed. The features of Zen as a spiritual and aesthetic practice in the West, the reasons for its spread and the specifics of the sympathetic audience are revealed. It was found that Zen Buddhism became a worldview platform for a significant jazz and subcultural environment, especially in the 60s of the XX century - the era of great objection and great refusal, the search for spiritual self-identity, the true sources of human transcendence, personal creative self-realization and ethical self-improvement. Passion for Zen, its meditative simplicity and routine of life has become a saving strategy for many representatives of creative and protest youth movements, an alternative spiritual resource for the intellectual elite of the West. It has been determined that these processes and phenomena have a specific borderline nature, which makes it possible, on the one hand, to organically and dynamically combine different characteristics and functions, on the other, to form new perspectives in the cultural environment. The simulative and technological nature of modern event industries and creative management in the context of new media, social networks, advertising business is outlined. An integrated approach in modern event technologies is presented: Tao-and-Zen-presentations based on restrained minimalist Zen aesthetics and Taoist principles of perception of life and the world. The openness, sincerity, and originality of these event actions are a potential prospect for the newest cultural industries and event management.