The intersection of machine learning and literary studies has brought about a revolutionary period of adaptation and creativity. The paper discusses the changing way we interact with canonical texts due to the progress of artificial intelligence (AI) and machine learning with an example of Shakespeare. Based on the stylometry, generative models, and data science analysis, the article examines how these technologies are transforming the creative processes, the authorship and the limits of adaptation. The research assesses the possibilities and constraints of AI-enabled adaptation through examples, critical reviews and direct textual illustrations, and concludes with the idea that such practices represent an ongoing conversation between human imagination and algorithmic creativity.