We present results from a project on sentiment analysis of drama texts, more concretely the plays of Gotthold Ephraim Lessing. We conducted an annotation study to create a gold standard for a systematic evaluation. The gold standard consists of 200 speeches of Lessing’s plays and was manually annotated with sentiment information by five annotators. We use the gold standard data to evaluate the performance of different German sentiment lexicons and processing configurations like lemmatization, the extension of lexicons with historical linguistic variants, and stop words elimination, to explore the influence of these parameters and to find best practices for our domain of application. The best performing configuration accomplishes an accuracy of 70%. We discuss the problems and challenges for sentiment analysis in this area and describe our next steps toward further research.