This article describes the process used to develop and assess an NSF-funded instructional innovation: an online collection (https://www.CAUSEweb.org/smiles/) of 28 interactive songs of high esthetic quality designed to span literature-based learning objectives of introductory statistics that develop statistical literacy and reasoning. The interactive songs are also designed to reduce statistics anxiety and require little time or instructor expertise. The songs are interactive in that the interface solicits (and provides hints and feedback on) student contributions (concepts or examples) and then plays back the song with student inputs integrated and highlighted. After providing a brief background, this article describes requirements, challenges, and opportunities in educational songwriting for the mathematical sciences, then describes the intervention and how its special nature affected the development process. Pilot studies at a research university and at a majority Black two-year college showed that students found the innovation to be a good tool to help their learning, reduce their anxiety about statistics, have an easy to follow interface, and use high quality songs. Analysis of log files from the use of the software shows some evidence of better performance on assessments after use and informs improvements of the automated feedback. Supplemental materials for this article are available online.