Physical likeness - for me this is probably the most enjoyable - if you follow some simple rules and ask yourself and others the questions the cartoonist asks himself every day. Silently ask yourself (in the presence of the sitter) what are the most distinguishing characteristics. Then ask yourself the same question later in with the sitter absent. Try and remember some aspect of the person like thick eyebrows, wavy hair, big ears etc.. Also try and remember a mannerism like, a pose, smile or use of hands; finally return to the sitter and experiment with some sketches. If nothing happens don't despair just keep trying and make some more simple sketches to help you. If all this doesn't work start your painting regardless!
The eyes - I make it a point of detailing the eyes (above in the portrait of Fletcher Christian as a young man). The eyes are the gateway to the visual world both for the viewer and the sitter. They must be as fine and detailed as you can achieve (unless the sitter is shy and for some reason seems to avoid looking directly). A few hints: widen the iris to give a more open and generous face. Add some flesh color to the whites and paint them as if they were pearls. They must appear round. Be subtle with the highlights. One eye is not the exact replica of the other. Make them a little different.
The hair - the hair usually separates the head from the background and should not be overworked. Only some small area showing some individual hair will suffice for an overal hairy effect.
The mouth - if the eyes are the visual gateway, the mouth could be said to be the emotional one - the enigmatic smile for instance. If the mouth does not obviously describe the sitters emotional disposition then the viewer is forced to look to the eyes. It is the trick of the Mona Lisa. Leonardo will not allow the viewers eye to settle. He keeps asking the question. Be careful with the little angles at the corners of the mouth - 45 degrees is the default.
The hands - adding the third element to the 'non-description' of the Mona Lisa are the hands - also in repose. No clue there either.
Note how, in creating substance, Leonardo does not define many edges - neither on the hands or the face.
The costume - sometimes I paint the costume before the hands, face and anything else. Then I save up my joy for later when detailing the folds, jewellery adornments etc. That part is relaxing and doesn't require the absolute concentration needed for flesh.
The background - here you can tell your story or make your narrative. For best practical results try and echo all the colors you have used for the flesh tones and costume in the background - just echoes in hue not value. Use value to make the narrative. See lesson on turning points.
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