Palaeontology developed as a field dependent upon comparison. Not only did reconstructing the fragmentary records of fossil organisms and placing them within taxonomic systems and evolutionary lineages require detailed anatomical comparisons with living and fossil animals, but the field also required thinking in terms of behavioural, biological and ecological analogies with modern organisms to understand how prehistoric animals lived and behaved. Yet palaeontological material often worked against making easy linkages, bringing a sense of mystery and doubt. This paper will look at an animal whose study exemplified these problems: the Chalicothere. Increasingly (although not unproblematically) recognized as a specific type from finds across North America and Eurasia from the early nineteenth century onwards, these prehistoric mammals showed short back legs terminating in pawed feet, long front limbs ending in sharp claws, a long flexible neck, and herbivorous grinding teeth. The Chalicothere became a significant organism within palaeontological studies, as the unexpected mix of characters made it a textbook example against the Cuvierian notion of "correlation of parts," while explaining how the animal moved, fed and behaved became puzzling. However, rather than prevent comparisons, these actually led to comparative analogies becoming flexible and varied, with different forms of comparison being made with varying methods and degrees of confidence, and with the anatomy, movement and behaviour of giraffes, bears, horses, anteaters, primates and other organisms all serving at various points as potential models for different aspects of the animal. This paper will examine some of the attempts to reconstruct and define the Chalicotheres across a long timescale, using this to show how multiple comparisons and analogies could be deployed in a reconstructive and evolutionary science like palaeontology, and illustrate some of the limits and tensions in comparative methods, as they were used to reconstruct organisms which were thought to be incomparable to any modern animal.