Can literature be investigated through quantitative methods? Can style, empathy, and prestige be measured? This study attempts to respond to these questions by providing results from a selection of case studies taken from German literature of the 19th through the 21st century, including Goethe’s late style, Felix Salten, and the output of contemporary writers such as Florian Meimberg’s twitterature and Daniel Glattauer’s e-mail novel. Altogether, this study shows how the interplay among literary theory, stylometry, stylistics, sentiment analysis, empirical studies, and archival research can offer new answers to old questions regarding German literature and provide tools to formulate new questions and novel approaches to research.