Considering that fairy tales have long been popular in second language (L2) education, we ask how these texts can remain applicable to our changing student body. In addition to their use in lower-level German classes for language and culture acquisition, fairy tales also provide a springboard into L2 literary interpretation for more advanced students, both at the secondary and postsecondary levels. The authors demonstrate that scaffolding and historical contextualization can enable students to engage in deep cultural and transcultural readings, public presentations, creative re-imaginings, as well as critical analyses. Examples come from two German programs at institutions with different educational goals--one focused on community-engagement, the other on diversity, equity, and inclusion (DEI). Both demonstrate how reading seminal tales through a variety of lenses can serve divergent learning goals. In one language program, they form the basis for community-engaged projects that connect learners to L2-speaking communities; in the other, they allow students to imagine social change by learning to recognize deep-seated inequities and critically examine how concepts of gender, race and ableism shape the spaces in which they live. The activities described are also applicable to other languages.