Recent advancements in NLP and machine learning have created unique challenges and opportunities for digital humanities research. In particular, there are ample opportunities for NLP and machine learning researchers to analyze data from literary texts and to broaden our understanding of human sentiment in classical Greek tragedy. In this paper, we will explore the challenges and benefits from the human and machine collaboration for sentiment analysis in Greek tragedy and address some open questions related to the collaborative annotation for the sentiments in literary texts. We focus primarily on (i) an analysis of the challenges in sentiment analysis tasks for humans and machines, and (ii) whether consistent annotation results are generated from the multiple human annotators and multiple machine annotators. For human annotators, we have used a survey-based approach with about 60 college students. We have selected three popular sentiment analysis tools for machine annotators, including VADER, CoreNLP’s sentiment annotator, and TextBlob. We have conducted a qualitative and quantitative evaluation and confirmed our observations on sentiments in Greek tragedy.