Thought this might be a fun collaborative/discussion thread. Even though the human form began appearing on coinage within about a century from its invention in the late 7th century BC, the Greeks mostly shied away from placing their rulers' porttaits on coinage, preferring to stick with icons and patron deities. This tradition was upheld until the death of Philip III and the subsequent implosion of Alexander's empire, when Ptolemy and Seleukos boldly placed their living image on their coinage as they wrestled for control with the other Diadochi. Portraiture would become standard fare for the Hellenistic world, and inspired one Roman Dictator in Perpetuity to do the same.... Ptolemy and Seleukos were not the first, however. While the Greeks of the classical age declined to appear on their coinage and the imperial Achaemenids opted for an idealized image of their semi-mythical founder, the western frontiers of the Persian Empire were ruled by powerful satraps who felt no binding taboo against showing their immediate subjects exactly who they paid their taxes to. I haven't ventured very far into this area of numismatics, but I do find it fascinating. Let's see your earliest coins bearing the mug of a living, breathing king, emperor, or satrap! First up is my least ambiguous, an obol of the Cilician satrap Tarkumuwa, better known by his Greek name Datames Cilicia, Tarsos AR obol of Datames 385-362 BC Obv: Head of Datames left in helmet, Aramaic TRKMW before Rev: Head of Arethusa, copying Kimon My others are all less certain. This one is certainly of a Cilician satrap, but nobody has been able to deduce who Another, possibly the same person? Possibly with his wife? (No longer my coin) These two are attributed to Pharnabazos (413-374 BC), predecessor and colleague of Datames, although not all are conviced the portrait is of him I argue that it is likely the case; compare the facial features to this one of the same ruler, depicting "Herakles with bare head" And finally, an enigmatic issue that may be one of the few coin portraits of a sitting Achaemenid emperor, although the jury is still out on whether this could be Artaxerxes II, Artaxerxes III, or merely Achamenes ("Great King") in Greek style Let's see some more early portraits!