The profound impact of Darwin's theory of evolution on biology has led to the acceptance of the theory in many complex systems that lie well beyond its original domain. Culture is one example that also exhibits key Darwinian evolutionary properties: Differential adoption of cultural variants (variation and selection), new entities imitating older ones (inheritance), and convergence toward the most suitable state (adaptation). In this work we present a framework for capturing the details of the evolutionary dynamics in cultural systems on the cultural product-level as interactors and the underlying replicators, "meme"-the cultural analog of the biological gene-level respectively. In the first part, we trace the cycle of prosperity-and-decline of a cultural product to find insights into influential and potent factors that determine its success. We propose quantitative parameters to characterize an on-chart life trajectory, and analyze a large-scale data set of songs from a major weekly Korean Pop chart. We find that a significant role is played by non-musical extrinsic factors, strongly indicative of the commodified nature of modern cultural products. In the second part, we analyze large-scale, comprehensive movie-meme association data to construct a timeline of the history of cinema via the evolution of genres and the rise and fall of prominent sub-genres. We also identify the impactful movies that were harbingers to popular memes that we may say correspond to the proverbial "Eve" of the human race, shining light on the process by which certain genres form and grow. Finally, we conclude the dissertation by measuring how the impact of movies correlates with the experts' and the public's assessment.