Quantifying the dissimilarity of two texts is an important aspect of a number of natural language processing tasks, including semantic information retrieval, topic classification, and document clustering. In this paper, we compared the properties and performance of different dissimilarity measures $D$ using three different representations of texts -- vocabularies, word frequency distributions, and vector embeddings -- and three simple tasks -- clustering texts by author, subject, and time period. Using the Project Gutenberg database, we found that the generalised Jensen--Shannon divergence applied to word frequencies performed strongly across all tasks, that $D$'s based on vector embedding representations led to stronger performance for smaller texts, and that the optimal choice of approach was ultimately task-dependent. We also investigated, both analytically and numerically, the behaviour of the different $D$'s when the two texts varied in length by a factor $h$. We demonstrated that the (natural) estimator of the Jaccard distance between vocabularies was inconsistent and computed explicitly the $h$-dependency of the bias of the estimator of the generalised Jensen--Shannon divergence applied to word frequencies. We also found numerically that the Jensen--Shannon divergence and embedding-based approaches were robust to changes in $h$, while the Jaccard distance was not.
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