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The history of Hollywood runs in tandem with the history of technological development. However, the digital revolution has transformed the film and TV industry in ways never foreseen. Hollywood studios have been forced to respond to the uncertainty – and potential for profit – prompted by the popularity of the internet and the success of new digital platforms, especially among young people. Thus, Hollywood is standing at a new crossroads, charted by two basic movements: on the one hand, the emergence of new windows for the exploitation of audiovisual products (linked to “long tail” markets; on the other, the consolidation of new type of consumer, known collectively as the i-generation or net-generation. The two related questions in this regard are: What new consumer habits define this emerging viewer/audience profile? As a consequence, what business model will rule this new digital scenario? This article tries to respond to both questions, tracing the framework of present and future challenges facing the entertainment industry. First, I will examine the defining features of the emerging consumer profile and address the most significant elements of the new digital economy, epitomized by the ‘long tail market’ model. Secondly, I will describe the Hollywood reaction to this new digital scenario and discuss the business models adopted by major American studios in relation to the downloading of films and TV programs. Finally, I will make some concluding remarks to reframe the changing face of the entertainment industry and the search for the right business strategies.