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I have drawn tens of thousands of smiles with teeth, but, if the teeth are bad, it is very hard to draw the portrait. I once had to draw an older gentleman from a photo which had bad teeth showing - REALLY BAD! I drew them as they were, impressionistically. The customer rejected the portrait, however, citing no specific reason. She later gave me a picture of the man without a smile. I redid the portrait, and she happily paid me.
I do not draw smiles anymore if the teeth are bad. (Most people do not smile with bad teeth anyway!)
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