The question why natural processes tend to flow along a preferred direction has always been considered from within the perspective of the Second Law of Thermodynamics, especially its statistical formulation due to Maxwell and Boltzmann. In this article, we re-examine the subject from the perspective of a new historico-philosophical formulation based on the careful use of selected theoretical elements taken from three key modern thinkers: Hans Reichenbach, Ilya Prigogine, and Roger Penrose, who are seldom considered together in the literature. We (...) emphasize in our analysis how the entropy concept was introduced in response to the desire to extend the applicability of the Second Law to the cosmos at large (Reichenbach and Penrose), and to examine whether intrinsic irreversibility is a fundamental universal characteristics of nature (Prigogine). While the three thinkers operate with vastly different technical proposals and belong to quite distinct intellectual backgrounds, some similarities are detected in their thinking. We philosophically examine these similarities but also bring into focus the uniqueness of each approach. Our purpose is not providing an exhaustive derivations of logical concepts identified in one thinker in terms of ideas found in the others. Instead, the main objective of this work is to stimulate historico-philosophical investigations and inquiries into the problem of the direction of time in nature by way of crossdisciplinary examinations of previous theories commonly treated in literature as disparate domains. (shrink)