This study delves into the evolution of the Indian Premier League, the world’s second-largest sports league, charting its transition from a niche to a mass cool brand. Through the lens of symbolic interactionism, it scrutinizes 13 years of the Indian Premier League’s promotional videos with 18 in-depth interviews of cultural intermediaries. The research spotlights the nuanced process of brand coolness within the Indian Premier League, demonstrating how the league’s brand identity undergoes a deliberate reconstruction, blending both traditional and modern sociocultural elements. A pivotal “boost cool” phase is identified, signaling a strategic shift to expand the brand’s appeal to a wider audience. This research contributes significantly to brand coolness literature by conceptualizing a brand coolness life cycle, charting a path from uncool, through niche and boost cool, to mass cool, and eventually to uncool or reinvention, highlighting “boost cool” as a critical transitional stage.