This piece of writing presents a dialogue with Nietzsche’s philosophy encompassing his entire documented life as a thinker, including his published works, posthumous fragments from different periods of his life, and letters that have philosophical content. In the book of his last period, “Ecce homo”, Nietzsche refers to himself as “the first tragical philosopher”. By “tragedy” he doesn’t mean a literal or purely aesthetic phenomenon, nor an artistic one if the art is understood in its average or/and usual meaning of “fine arts”. Accordingly, art for him isn’t meant even as the common craft, the skill, or ingenuity of producing “things” (gr. τέχνη, ποίησις) from non-existence to existence. The art itself is from the perspective of the artist “the great stimulant of life”, drunkenness, inebriation in the meaning of enthusiasm for life as a problematic, doubtful and dangerous challenge, rather than comfort, security and enjoyment. It is also a state of the highest creative sobriety, though in its root sheer erotic power. Erotic inebriation as the highest form of life transfiguration through Dionysian ecstasy finds its highest form in the tragical art. That is the reason why Nietzsche’s philosophy in the foundation has a tragical character. For Nietzsche, the main event of the Occident (not history, which can only be derivative, scientific knowledge and tale of the past) has also a tragical, occidental form, in the meaning of downfall. The word “nihilism” means not somebody's negative opinion of the current state of affairs, but the insight in the “logic” of the will for power, which in the age of old values declined to will for nothingness. That basic event of the Western world, which began in ancient Greece, and today has become global, can be overcome only by meditation on the primal event of the Occident, which is the most transparent in the tragical passion and drama. The words commonly used to express the meaning of the Greek words "πάθος" and “δρᾶμα“ are not philosophically nor philologically suitable. Due to philosophical necessity, German and Slavic variants require different translations, which in a play of words in English can be only described. The tragic spirit is opposed by the scientific spirit, while philosophy itself, within its reflection, and leads a constant struggle between these two aspirations. This work attempts to show the relationship between art, philosophy and science in the context of a specific philosophical conversation that is understood historically, i.e. as a one-time event and in ultimate individuality. In his first published work, "The Birth of Tragedy," Nietzsche explores the idea of the tragic determination of Eros, which remains a decisive factor in his opinion. He believed that the scientific spirit is opposed to the tragic spirit, and that there is a constant struggle between these two aspirations in philosophy. This paper aims to explore the relationship between art, philosophy, and science in the context of a specific philosophical conversation, which is understood historically as a unique and individual event. This implies that the spiritual manifestations of philosophia perennis or ars perennis do not exist, and that these should be considered in their finitude and eternity, as Nietzsche also believed. The relationship between philosophy and art, particularly how Friedrich Nietzsche viewed this relationship, as well as the impact of ancient philosophy and art on contemporary philosophy are the subjects of many studies and interpretations. These topics are explored in various fields including philosophy, philology, and other relevant humanities. This work provides a critical analysis of the dominant interpretations and perspectives of previous studies and presents a new understanding of Nietzsche's views on the tragic as it was portrayed in early Greek culture. Through this approach, a new interpretation of the essence of Nietzsche's philosophy is offered, which significantly enhances our understanding of Nietzsche's relevance in contemporary philosophy. The philosophical contribution of the paper is the clarification of known aspects of Nietzsche's thinking and the discovery of factors that remain neglected or little explored in the known literature. The question of the essence of Greek tragedy is still of primary importance today, perhaps even more so than Nietzsche's time. The effort to show beyond the duality of infinity and mere limitation the original sense of finitude (measure) seems to us to be crucial for understanding both Nietzsche and the Greeks. The relationship between philosophy and art, including especially the way Friedrich Nietzsche thought about this relationship, as well as the reception of ancient philosophy and art in contemporary philosophy, is the subject of numerous researches and interpretations in the world, but also in our philosophy and philology, and partly in other relevant humanistic sciences. Through the work, the dominant tendencies and directions of the previous interpretations are critically re-examined, and a new view of Nietzsche's reception of the tragic as it was profiled in the earliest periods of Greek culture is offered. Through this perspective, a new interpretation of the essence of Nietzsche's philosophy is given, which represented a significant enrichment of insight into the meaning of Nietzsche for contemporary philosophy. The aim of this work is to interpret the original text for the purpose of philosophical conversation. It also aims to analyze Nietzsche's historical place in the history of philosophy and Western civilization, which has its roots in ancient Greece. The work covers three levels of study. The first level involves the interpretation of Nietzsche's opinion and its relationship to the opinions expressed in the works of Greek poets and thinkers. This leads to the second level of inquiry, which is to understand the meaning of tragedy, science, and philosophy. Finally, the third level of investigation pertains to contemporary questions about the fate of philosophy, science, technology, and the modern world. The purpose of this paper is to demonstrate that Nietzsche's understanding of the tragic as Dionysian is present in all the major principles of his philosophy, including ontology, philosophy of history, and history of philosophy. Additionally, it is illustrated how this understanding is manifested in a practical sense, and how it remains in the same spiritual context as his relationship with Greek and other philosophers. The basic assumption is that a philosophical conversation can be had in a historical context. Despite the apparent variation in opinions among great thinkers, there is a fundamental commonality even in the midst of controversy.