This chapter embarks on an engrossing journey, unravelling the transformational landscape of OTT media. It traces its humble beginnings to its disruptive force in the entertainment industry, exploring the impact on traditional media models. With on-demand content and cord-cutting on the rise, traditional broadcasters face challenges. Global expansion brings localized content and fierce competition between players, while technological innovations enhance user experiences with AI-driven personalization, VR, and AR. As the future of OTT unfolds, emerging business models and cutting-edge tech promise boundless possibilities. Understanding its historical context is vital, paving the way for an ever-evolving world of captivating entertainment.