The question of methodology in cultural science was a central concern for neo-Kantian philosophers at the beginning of the 20th century, which foregrounds Critical Theory. This paper examines how Georg Lukács and Walter Benjamin approached this question in their respective works, Theory of the Novel and Origin of the German Trauerspiel. Lukács’ work laid the foundation by identifying the a priori condition of modern experience, characterized by his concept of transcendental homelessness. However, his formalist approach lacked a rigorous methodology for accessing these conditions. Benjamin, drawing on Hermann Cohen’s transcendental method, sought to overcome this limitation by developing the concept of origin. Origin, for Benjamin, refers to the process of thinking that responds to the historical conditions of experience, which can be accessed through the analysis of aesthetic forms. By tracing the development of their investigation of modern conditions of experience from Lukács to Benjamin, the essay argues that their shared project aligns with a historical science of modernity that avoids both metaphysical speculation and positivistic reduction. Combining Lukács’ problematics and Cohen’s transcendental method, Benjamin’s aforementioned work presents a unique solution to this methodological problem, enabling a philosophically grounded approach to the study of cultural phenomena in their historical specificity.