We posit that a key factor in how effective songs are in students' motivation, engagement, and learning is how interactive the song experience is for students. We articulate and tour a continuum of interactivity, illustrated with examples that are grounded in the context of core learning objectives in mathematics and statistics for students in high school or college, but applicable to virtually any subject matter. Our current NSF-funded Project SMILES (Student Made Interactive Learning with Educational Songs for introductory statistics), loosely inspired by the Mad LibsTM phrasal word template game, has high interactivity by having students supply pre-song inputs (contextual examples or conceptual connections) that prime them to learn from the ensuing song -- a song which is readily played back to them with their inputs! I will discuss an example from Project SMILES, whose effectiveness is being assessed this year by randomized experiments coordinated by my fellow grant PIs Dennis Pearl and John Weber. The big picture tour (which incorporates audience polling questions!) will be followed by lively discussion tailored to VOICES attendees' interests. We also share references and resources for exploration beyond this session.