I remember an experience I had when I first started collecting ancient coins. I used to visit the shop of a local coin dealer every month or so, just checking to see what new stuff had come in. One time he handed me a coin of Constantine the Great and said, "Doesn't this coin have a great portrait?" I looked at the coin and saw the same head facing to the right that I always saw, (see photo,) but I mumbled something polite, smiled, and handed back the coin."How can a coin be said to have a 'great portrait' when they all basically look alike?" I wondered. Well, as most seasoned coin collectors can tell you, eye appeal is one of the most important factors in determining the desirability (and therefore monetary value) of a coin. And since the portrait is the focal point of most coins, it stands to figure that a "great portrait" would be an asset to a coin. Ancient coins were each struck individually by hand, so no two ancient coins are ever exactly alike, and so finding that one coin has a "great portrait" while another has an "average portrait" makes a certain amount of sense, even to the novice coin collector, once she thinks about it for a little while. But when you start seeing "great portraits" on individual U.S. Lincoln Cents, you know you're hooked on coin collecting!
The portrait on a coin tells us a lot about the coin. For more than two millennia, the portrait has been the sort of "imprimatur," or proof of genuineness, that even the illiterate peasant who couldn't read the lofty inscriptions could accept. The portrait usually tells us which side of the coin is the obverse. Oftentimes, the portrait serves to provide continuity when the coin designs change frequently, such as the Washington portrait on U.S. Statehood Quarters. Even if you've never seen the new state-specific reverse before, you'd know the coin was a U.S. Quarter Dollar because of the familiar portrait of Washington each Statehood Quarter bears.
I have some interesting details about the portraits on coins. Check out: Photo of coin of Constantine the Great courtesy of Harlan J. Berk, Ltd. (And for the record, this specimen has only an average portrait.) ;)

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