Bizzare Horse

So many things are going on in the one creature. Its  a horse that is flaming witha beard and a unicorn horn… yes thats a thing.

(aD&D Fiend Folio)

Literally Crabman

Love it! Although I initially thought it was a lobster…
AD&D 2e

Slice of History

The back of the ad&d 2nd edition players hand book. 

Hair

Im jelous of that fine pony tail.

MM2 3.0

Little Man Staff

He look very sullen.
Advance Players Guide – Pathfinder

Dungeons and Dinos

MM2 3.0

Sad Beast

It looks sad and scared. Its a scary design with the large eye and pincers but the fear is gone as it looks like its crying.