The Chalicotheres were among the strangest ungulates to ever live. Possessing vaguely horselike heads, gorillalike body proportions and slothlike claws, these animals were formerly successful browsing herbivores. Emerging during the Middle Eocene roughly 48 million years ago, basal Chalicotheres closely resembled other Perissodactyls of the time. However, the more derived family Chalicotheriidae developed the clawed feet typical of the group. Members of this lineage ranged sheep to draft horse sized. By the Late Oligocene, two notable subfamilies had diverged, with these being the Chalicotheriines and Schizotheriines.

The former possessed highly elongated forelimbs, stout hindlimbs and walked on their knuckles in order to keep their claws off the ground. The latter had more typical ungulate proportions, although had also developed retractable claws, walking in a digitigrade stance. Chalicotheres thrived across Africa, Eurasia and North America during the Miocene, although entered a period of decline in the Pliocene. This was probably due to the cooling and drying conditions of the time reducing their favored forested habitats. The youngest genera were the Chalicotheriines Hesperotherium and Nestoritherium, which were native to China and South East Asia until the Middle Pleistocene about 780,000 years.

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