The cutest historical depiction of prehistoric animals? Where "chibi-fied" Ichthyosaur, Plesiosaur, Megalosaur and Pterodactyl scrutinise reconstruction of a human. Made for Natural History Museum London by Thomas De la Ruei, 19th century.
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Since you seem to have your hand on more humorous/anthropomorphized paleoart. I'm trying to find a copy of William E. Scheele's "At the K-T Boundary Bar and Grille". It disappeared from the wall outside the gift shop at the Cleveland Museum of Natural History when they reconstructed the place.
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They're kinda like cats. They're definitely of yore.