Digital media and literature have long been combined in various ways, such as enriching the image by adding video and music to literary works that could only be enjoyed through text media. In this paper, I would like to explore Shakespeare’s Romeo and Juliet through movies and pop music. The legendary love stories of teenage lovers whose fate has been broken are being interpreted and re-examined from various angles from a modern perspective. Also, through this paper, I would like to study that shakespeare’s works are not limited to socially or educated classes defined in a narrow sense or narrowly defined form of performance, but are replaced by cultural artifacts that can be used by everyone to actively support Shakespeare’s popularity. Shakespeare is one of the most popular and fastest growing research agendas in mass media, especially movies, videos and television. In the future, we must accept Shakespeare as a method, not just a topic. Performing world-class Shakespeare through movies, stage performances, and festivals can produce the production of cultural liquidity that travels beyond its limits from its own habitat with the help of popular music. Just as Shakespeare is ubiquitous in popular culture, people are facing Shakespeare’s tradition of research need to interpret Shakespeare’s values newly.