Society and current events shape the art of their time. Many works of operatic and song literaturethat are considered masterpieces have elements that are challenging to modern audiences–be it their composer’s personal beliefs, embedded racism and sexism, or other unfavorable aspects. How to deal with these controversial elements of standard repertoire is not wholly agreed upon and the divide on how to engage with them is often generational. Those of an older generation often espouse the inherent value of these works, whereas those of a younger generation struggle to see beyond their faults. This does not have to divide the classical world of singing–with sincere and careful thought, discussion, and research it is possible to engage with works that have a checkered past and to continue to grow the canon and our understanding of it. Supplementing materials accompanying this dissertation project including video recordings of each performance event.