We present results of a sentiment annotation study in the context of historical German plays. Our annotation corpus consists of 200 representative speeches from the German playwright Gotthold Ephraim Lessing. Six annotators, five non-experts and one expert in the domain, annotated the speeches according to different sentiment annotation schemes. They had to annotate the differentiated polarity (very negative, negative, neutral, mixed, positive, very positive), the binary polarity (positive/negative) and the occurrence of eight basic emotions. After the annotation, the participants completed a questionnaire about their experience of the annotation process; additional feedback was gathered in a closing interview. Analysis of the annotations shows that the agreement among annotators ranges from low to mediocre. The non-expert annotators perceive the task as very challenging and report different problems in understanding the language and the context. Although fewer problems occur for the expert annotator, we cannot find any differences in the agreement levels among non-experts and between the expert and the non-experts. At the end of the paper, we discuss the implications of this study and future research plans for this area.