Shakespeare is often a hurdle over which many of our students must “fall down, or else o'erleap” as his works endure as standard core texts across many grade and ability levels of high school English. Yet, despite his popularity amongst English scholars, teachers, and curriculum administrators, Shakespeare remains most unpopular with our students—especially amongst our reluctant readers. To bridge the gap, we must ask ourselves: how can we engage reluctant readers with these challenging 400-year-old plays? This thesis will delineate my experiences exploring three avenues of student engagement with the Bard’s work in my tenth grade English classroom including media and technology, writing, and physical performance.