This study intended to explore how a web 2.0 tool, Scoop.it, could be used to curate and differentiate web-based content within the context of teaching a Shakespearean tragedy, King Lear, and devise a personal and professional learning environment for instructional use. The study also aims to understand how Wolff and Mulholland’s Curatorial Inquiry Learning Cycle could be instrumental in the analysis and interpretation of curated content, within and across types of web-based sources, to inform instructional planning. The researcher focused on the following types of sources: blogs, comics, presentations, videos, trailers, works of art, reviews, podcasts and wikis, and the Curatorial Inquiry Learning Cycle facilitated purposeful and systematic curation of content. Initial curation and analysis of content provided second-order interpretations about each source type around a priori themes of the play. To enable interpretation across source types, the researcher adapted Gustav Freytag’s Pyramid of Dramatic Structure, and provided third-order interpretations for instructional use.