The Bengali film industry, based in Kolkata (Tollywood), has produced a century-long legacy of cinematic artistry. Central to this legacy is the figure of the Bengali actress, whose role has shifted dramatically from a mythological ideal to a contemporary, multi-platform content creator. This paper examines the evolution of the Kolkata Bangla actress within the ecosystem of popular media, analyzing her trajectory from the "village belle" of the 1950s–70s to the urban professional of the 2000s, and finally to the digital-first influencer of the 2020s. It argues that while mainstream commercial cinema continues to define star hierarchies, the rise of Over-The-Top (OTT) platforms, YouTube web series, and lifestyle social media has democratized content creation, empowered actresses with narrative agency, and fundamentally reshaped audience engagement. The paper concludes by exploring persistent challenges, including gender-based typecasting and the pressures of digital surveillance.