The enigma of black holes has captured human imagination and scientific curiosity for decades, engendering both awe and trepidation. These celestial entities are not merely abstract equations sketched on a chalkboard; they are real, complex phenomena that confront our most basic intuitions about the universe. Beyond their immense gravitational pull and beguiling event horizons, black holes are intricate puzzles that require the most sophisticated tools in physics, astronomy, and even philosophy to understand. The aim of this book, "The Story of Black Holes From Collapsing Stars to Cosmic Paradoxes:," is to provide a comprehensive yet accessible examination of black holes and their enigmatic cousins—naked singularities. By delving into the heart of these cosmic phenomena, this volume takes readers on a journey that starts with the observable universe and ends in the depths of quantum gravity. We explore not only the astrophysics of black holes but also the philosophical implications of their existence and their representation in popular culture. To embark on this multidisciplinary exploration, the book has been divided into twenty meticulously designed chapters, each focusing on a specific aspect of black holes or the universe at large. From the cosmic stage set by the observable universe and the Big Bang theory to the exotic terrains of quantum fluctuations near black holes, this book encapsulates the spectrum of existing knowledge and lingering questions in modern astrophysics and cosmology.